US9616394B2 - Graft copolymer functionalized article - Google Patents
Graft copolymer functionalized article Download PDFInfo
- Publication number
- US9616394B2 US9616394B2 US14/400,810 US201314400810A US9616394B2 US 9616394 B2 US9616394 B2 US 9616394B2 US 201314400810 A US201314400810 A US 201314400810A US 9616394 B2 US9616394 B2 US 9616394B2
- Authority
- US
- United States
- Prior art keywords
- substrate
- group
- meth
- monomer
- ligand
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active, expires
Links
- 229920000578 graft copolymer Polymers 0.000 title abstract description 6
- 239000000758 substrate Substances 0.000 claims abstract description 172
- -1 Guanidinyl Chemical group 0.000 claims abstract description 101
- 238000000034 method Methods 0.000 claims abstract description 82
- 229920000642 polymer Polymers 0.000 claims abstract description 59
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 19
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 19
- 241000700605 Viruses Species 0.000 claims abstract description 9
- 150000007523 nucleic acids Chemical class 0.000 claims abstract description 9
- 102000039446 nucleic acids Human genes 0.000 claims abstract description 9
- 108020004707 nucleic acids Proteins 0.000 claims abstract description 9
- 239000002158 endotoxin Substances 0.000 claims abstract description 8
- 241000894006 Bacteria Species 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 140
- 239000003446 ligand Substances 0.000 claims description 49
- 241000894007 species Species 0.000 claims description 44
- 229920000768 polyamine Polymers 0.000 claims description 38
- 229920001577 copolymer Polymers 0.000 claims description 33
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000000524 functional group Chemical group 0.000 claims description 25
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 18
- 239000012965 benzophenone Substances 0.000 claims description 18
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 239000012530 fluid Substances 0.000 claims description 12
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 11
- 108090000790 Enzymes Proteins 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 10
- 229920002873 Polyethylenimine Polymers 0.000 claims description 10
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000000412 dendrimer Substances 0.000 claims description 6
- 229920000736 dendritic polymer Polymers 0.000 claims description 6
- 239000013060 biological fluid Substances 0.000 claims description 4
- 230000002906 microbiologic effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 108010039918 Polylysine Proteins 0.000 claims description 3
- 238000004113 cell culture Methods 0.000 claims description 3
- 238000000855 fermentation Methods 0.000 claims description 3
- 230000004151 fermentation Effects 0.000 claims description 3
- 229920000656 polylysine Polymers 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 241000203069 Archaea Species 0.000 claims description 2
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 abstract description 20
- 238000000576 coating method Methods 0.000 abstract description 20
- 239000012620 biological material Substances 0.000 abstract description 15
- 230000007935 neutral effect Effects 0.000 abstract description 6
- 229920001002 functional polymer Polymers 0.000 abstract description 5
- 239000000243 solution Substances 0.000 description 60
- 239000012528 membrane Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 25
- 229940098773 bovine serum albumin Drugs 0.000 description 25
- 239000002585 base Substances 0.000 description 19
- 239000000835 fiber Substances 0.000 description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- 230000003068 static effect Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000011148 porous material Substances 0.000 description 10
- 238000002145 thermally induced phase separation Methods 0.000 description 10
- 239000004677 Nylon Substances 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 229920001778 nylon Polymers 0.000 description 9
- 0 *N([3*])/C(=N/[3*])N([3*])[2*]CC(=O)C([1*])=C.C.[1*]C(=C)C(=O)C[2*]C([5*])=NN([3*])/C(=N\[3*])N([3*])[4*] Chemical compound *N([3*])/C(=N/[3*])N([3*])[2*]CC(=O)C([1*])=C.C.[1*]C(=C)C(=O)C[2*]C([5*])=NN([3*])/C(=N\[3*])N([3*])[4*] 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000012472 biological sample Substances 0.000 description 6
- 125000005549 heteroarylene group Chemical group 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 125000003010 ionic group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- 239000012815 thermoplastic material Substances 0.000 description 5
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000012982 microporous membrane Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 102000016943 Muramidase Human genes 0.000 description 3
- 108010014251 Muramidase Proteins 0.000 description 3
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229940093476 ethylene glycol Drugs 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000004325 lysozyme Substances 0.000 description 3
- 229960000274 lysozyme Drugs 0.000 description 3
- 235000010335 lysozyme Nutrition 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 2
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 2
- NBNBTPCBNOFEDT-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazin-6-one Chemical compound C=CC1=NCCC(=O)O1 NBNBTPCBNOFEDT-UHFFFAOYSA-N 0.000 description 2
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 229920001222 biopolymer Polymers 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000007156 chain growth polymerization reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000010981 drying operation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 229920000587 hyperbranched polymer Polymers 0.000 description 2
- 229920000831 ionic polymer Polymers 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- 229920000083 poly(allylamine) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000011045 prefiltration Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000037452 priming Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000004080 punching Methods 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000007155 step growth polymerization reaction Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- UIXMDLKLTFVYKN-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) prop-2-enoate Chemical compound ClC(=O)C(C)OC(=O)C=C UIXMDLKLTFVYKN-UHFFFAOYSA-N 0.000 description 1
- SQTUYFKNCCBFRR-UHFFFAOYSA-N (2,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(OC)=C1 SQTUYFKNCCBFRR-UHFFFAOYSA-N 0.000 description 1
- NIBPGNKODUOZIW-UHFFFAOYSA-M (2-hydroxy-3-prop-2-enoyloxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)COC(=O)C=C NIBPGNKODUOZIW-UHFFFAOYSA-M 0.000 description 1
- UILJLCFPJOIGLP-BYPYZUCNSA-N (2s)-2-(prop-2-enoylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)C=C UILJLCFPJOIGLP-BYPYZUCNSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- KLQFGGPGAIXZTF-UHFFFAOYSA-N (5-oxo-4h-1,3-oxazol-2-yl) prop-2-enoate Chemical compound C=CC(=O)OC1=NCC(=O)O1 KLQFGGPGAIXZTF-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GFNDFCFPJQPVQL-UHFFFAOYSA-N 1,12-diisocyanatododecane Chemical compound O=C=NCCCCCCCCCCCCN=C=O GFNDFCFPJQPVQL-UHFFFAOYSA-N 0.000 description 1
- HSGQMLDRUDGOQE-UHFFFAOYSA-N 1,3,5-triisocyanatocyclohexane Chemical compound O=C=NC1CC(N=C=O)CC(N=C=O)C1 HSGQMLDRUDGOQE-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- ZEIXNMVAJQLPMA-UHFFFAOYSA-N 1-ethenyl-4-isocyanatobenzene Chemical compound C=CC1=CC=C(N=C=O)C=C1 ZEIXNMVAJQLPMA-UHFFFAOYSA-N 0.000 description 1
- LYDHLGJJJAWBDY-UHFFFAOYSA-N 1-isocyanato-4-[2-(4-isocyanatocyclohexyl)propan-2-yl]cyclohexane Chemical compound C1CC(N=C=O)CCC1C(C)(C)C1CCC(N=C=O)CC1 LYDHLGJJJAWBDY-UHFFFAOYSA-N 0.000 description 1
- JNMJIXITXWBDMJ-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetrakis(oxiran-2-ylmethyl)benzene-1,3-diamine Chemical compound C1OC1CN(C=1C=C(C=CC=1)N(CC1OC1)CC1OC1)CC1CO1 JNMJIXITXWBDMJ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- UVDYBBRVDUKNFV-UHFFFAOYSA-N 2-(prop-2-enoylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC(=O)C=C UVDYBBRVDUKNFV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- YFBQXUGQIFAFMM-UHFFFAOYSA-N 2-chloro-n-methylethanamine Chemical compound CNCCCl YFBQXUGQIFAFMM-UHFFFAOYSA-N 0.000 description 1
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-UHFFFAOYSA-N 0.000 description 1
- QKPKBBFSFQAMIY-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC1(C)N=C(C=C)OC1=O QKPKBBFSFQAMIY-UHFFFAOYSA-N 0.000 description 1
- VXUVJQIYKFXQMR-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-5h-1,3-oxazin-6-one Chemical compound CC1(C)CC(=O)OC(C=C)=N1 VXUVJQIYKFXQMR-UHFFFAOYSA-N 0.000 description 1
- DMDNNZDDQOLFPX-UHFFFAOYSA-N 2-ethenyl-4-ethyl-4-methyl-1,3-oxazol-5-one Chemical compound CCC1(C)N=C(C=C)OC1=O DMDNNZDDQOLFPX-UHFFFAOYSA-N 0.000 description 1
- DPODNGMCVCYGFM-UHFFFAOYSA-N 2-ethenyl-4-methyl-4h-1,3-oxazol-5-one Chemical compound CC1N=C(C=C)OC1=O DPODNGMCVCYGFM-UHFFFAOYSA-N 0.000 description 1
- HXVJTLFCFCSHHM-UHFFFAOYSA-N 2-ethenyl-4h-1,3-oxazol-5-one Chemical compound C=CC1=NCC(=O)O1 HXVJTLFCFCSHHM-UHFFFAOYSA-N 0.000 description 1
- NLFVKNZCTVNNIJ-UHFFFAOYSA-N 2-ethenyl-5,6-dihydro-4h-1,3-oxazepin-7-one Chemical compound C=CC1=NCCCC(=O)O1 NLFVKNZCTVNNIJ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- NEYTXADIGVEHQD-UHFFFAOYSA-N 2-hydroxy-2-(prop-2-enoylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)C=C NEYTXADIGVEHQD-UHFFFAOYSA-N 0.000 description 1
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 1
- VSSGDAWBDKMCMI-UHFFFAOYSA-N 2-methyl-2-(2-methylprop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)NC(C)(C)CS(O)(=O)=O VSSGDAWBDKMCMI-UHFFFAOYSA-N 0.000 description 1
- JEHFRMABGJJCPF-UHFFFAOYSA-N 2-methylprop-2-enoyl isocyanate Chemical compound CC(=C)C(=O)N=C=O JEHFRMABGJJCPF-UHFFFAOYSA-N 0.000 description 1
- MEAHFJBYWLCGDM-UHFFFAOYSA-N 2-pentadecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCCC(C(O)=O)C(O)=O MEAHFJBYWLCGDM-UHFFFAOYSA-N 0.000 description 1
- QKYWQDWJDQHBPI-UHFFFAOYSA-N 2-prop-1-en-2-yl-4h-1,3-oxazol-5-one Chemical compound CC(=C)C1=NCC(=O)O1 QKYWQDWJDQHBPI-UHFFFAOYSA-N 0.000 description 1
- ZKFOEDSYSPDTEB-UHFFFAOYSA-N 2-prop-2-enoyloxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C=C ZKFOEDSYSPDTEB-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- QMAQLCVJIYANPZ-UHFFFAOYSA-N 2-propoxyethyl acetate Chemical compound CCCOCCOC(C)=O QMAQLCVJIYANPZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- DQRFCVHLNUNVPL-UHFFFAOYSA-N 2h-1,3-oxazol-5-one Chemical compound O=C1OCN=C1 DQRFCVHLNUNVPL-UHFFFAOYSA-N 0.000 description 1
- BPLZPLKYBMLWGU-UHFFFAOYSA-N 3-(4-benzoylphenoxy)propane-1-sulfonic acid Chemical compound C1=CC(OCCCS(=O)(=O)O)=CC=C1C(=O)C1=CC=CC=C1 BPLZPLKYBMLWGU-UHFFFAOYSA-N 0.000 description 1
- AMIULHAFCHLPIK-UHFFFAOYSA-N 3-(9-oxothioxanthen-2-yl)oxypropane-1-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(OCCCS(=O)(=O)O)=CC=C3SC2=C1 AMIULHAFCHLPIK-UHFFFAOYSA-N 0.000 description 1
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 1
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 description 1
- YVAQHFNMILVVNE-UHFFFAOYSA-N 3-(prop-2-enoylamino)propanoic acid Chemical compound OC(=O)CCNC(=O)C=C YVAQHFNMILVVNE-UHFFFAOYSA-N 0.000 description 1
- LLTAGRBKLBDOIZ-UHFFFAOYSA-N 3-(tert-butylamino)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCNC(C)(C)C LLTAGRBKLBDOIZ-UHFFFAOYSA-N 0.000 description 1
- FLBUPMRFQUKGBK-UHFFFAOYSA-N 3-(tert-butylamino)propyl prop-2-enoate Chemical compound CC(C)(C)NCCCOC(=O)C=C FLBUPMRFQUKGBK-UHFFFAOYSA-N 0.000 description 1
- ALOVNINORQGNGW-UHFFFAOYSA-N 3-[methyl(prop-2-enoyl)amino]propanoyl chloride Chemical compound C=CC(=O)N(C)CCC(Cl)=O ALOVNINORQGNGW-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- MUWZQYSJSCDUDT-UHFFFAOYSA-N 4,4-dimethyl-2-prop-1-en-2-yl-1,3-oxazol-5-one Chemical compound CC(=C)C1=NC(C)(C)C(=O)O1 MUWZQYSJSCDUDT-UHFFFAOYSA-N 0.000 description 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- MIFGCULLADMRTF-UHFFFAOYSA-N 4-[(4-hydroxy-3-methylphenyl)methyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C=C(C)C(O)=CC=2)=C1 MIFGCULLADMRTF-UHFFFAOYSA-N 0.000 description 1
- UHUUGQDYCYKQTC-UHFFFAOYSA-N 4-[2,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CC(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UHUUGQDYCYKQTC-UHFFFAOYSA-N 0.000 description 1
- HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 description 1
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- KVDIYEZFYBIHRN-UHFFFAOYSA-N 4-methyl-2-prop-1-en-2-yl-4h-1,3-oxazol-5-one Chemical compound CC1N=C(C(C)=C)OC1=O KVDIYEZFYBIHRN-UHFFFAOYSA-N 0.000 description 1
- PCEYDYZJGXEYTA-UHFFFAOYSA-N 5,5-bis(2-methylphenyl)-2-prop-1-en-2-yl-4h-1,3-oxazin-6-one Chemical compound O=C1OC(C(=C)C)=NCC1(C=1C(=CC=CC=1)C)C1=CC=CC=C1C PCEYDYZJGXEYTA-UHFFFAOYSA-N 0.000 description 1
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- MUNIMTADWFHKOO-UHFFFAOYSA-L C(C=C)(=O)NC(C)(C(=O)NCCCCNC(=N)N)C.S(=O)(=O)([O-])[O-].[Na+].[Na+] Chemical compound C(C=C)(=O)NC(C)(C(=O)NCCCCNC(=N)N)C.S(=O)(=O)([O-])[O-].[Na+].[Na+] MUNIMTADWFHKOO-UHFFFAOYSA-L 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 239000007993 MOPS buffer Substances 0.000 description 1
- LZCXCXDOGAEFQX-UHFFFAOYSA-N N-Acryloylglycine Chemical compound OC(=O)CNC(=O)C=C LZCXCXDOGAEFQX-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920001054 Poly(ethylene‐co‐vinyl acetate) Polymers 0.000 description 1
- 229920001744 Polyaldehyde Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 108010008281 Recombinant Fusion Proteins Proteins 0.000 description 1
- 102000007056 Recombinant Fusion Proteins Human genes 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- LOPVAWVHGAWUPS-UHFFFAOYSA-M [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]-trimethylazanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC(O)C[N+](C)(C)C LOPVAWVHGAWUPS-UHFFFAOYSA-M 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QDHUQRBYCVAWEN-UHFFFAOYSA-N amino prop-2-enoate Chemical class NOC(=O)C=C QDHUQRBYCVAWEN-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 238000003705 background correction Methods 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229960000074 biopharmaceutical Drugs 0.000 description 1
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- ZXOATMQSUNJNNG-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OCC2OC2)=CC=1C(=O)OCC1CO1 ZXOATMQSUNJNNG-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical compound CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000005465 channeling Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
- UORKIKBNUWJNJF-UHFFFAOYSA-N chrysene-1,4-dione Chemical compound C1=CC2=CC=CC=C2C(C=C2)=C1C1=C2C(=O)C=CC1=O UORKIKBNUWJNJF-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011118 depth filtration Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- NVLHKSGUMYMKRR-UHFFFAOYSA-N dodeca-2,10-dienediamide Chemical compound NC(=O)C=CCCCCCCC=CC(N)=O NVLHKSGUMYMKRR-UHFFFAOYSA-N 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- IQIJRJNHZYUQSD-UHFFFAOYSA-N ethenyl(phenyl)diazene Chemical compound C=CN=NC1=CC=CC=C1 IQIJRJNHZYUQSD-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 125000004474 heteroalkylene group Chemical group 0.000 description 1
- PKNLWLCURZNADF-UHFFFAOYSA-N hex-5-enoyl chloride Chemical compound ClC(=O)CCCC=C PKNLWLCURZNADF-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UZLGVMYVDYNSCS-UHFFFAOYSA-M methyl sulfate;trimethyl(2-prop-2-enoyloxyethyl)azanium Chemical compound COS([O-])(=O)=O.C[N+](C)(C)CCOC(=O)C=C UZLGVMYVDYNSCS-UHFFFAOYSA-M 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- GUAQVFRUPZBRJQ-UHFFFAOYSA-N n-(3-aminopropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCN GUAQVFRUPZBRJQ-UHFFFAOYSA-N 0.000 description 1
- FZLUWDXMHJPGBS-UHFFFAOYSA-N n-(3-aminopropyl)prop-2-enamide Chemical compound NCCCNC(=O)C=C FZLUWDXMHJPGBS-UHFFFAOYSA-N 0.000 description 1
- VAUOPRZOGIRSMI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)aniline Chemical class C1OC1CNC1=CC=CC=C1 VAUOPRZOGIRSMI-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- RNLCQTGFIMNBPT-UHFFFAOYSA-N n-[2-(1h-imidazol-2-yl)ethyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCC1=NC=CN1 RNLCQTGFIMNBPT-UHFFFAOYSA-N 0.000 description 1
- ZJGCZHVHVKODLC-UHFFFAOYSA-N n-[3-(1h-benzimidazol-2-yl)propyl]-2-methylprop-2-enamide Chemical compound C1=CC=C2NC(CCCNC(=O)C(=C)C)=NC2=C1 ZJGCZHVHVKODLC-UHFFFAOYSA-N 0.000 description 1
- AZZNUMLQDSAWOK-UHFFFAOYSA-N n-[3-(1h-benzimidazol-2-yl)propyl]prop-2-enamide Chemical compound C1=CC=C2NC(CCCNC(=O)C=C)=NC2=C1 AZZNUMLQDSAWOK-UHFFFAOYSA-N 0.000 description 1
- VTEAUZAMSJACBW-UHFFFAOYSA-N n-[3-(1h-imidazol-2-yl)propyl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCC1=NC=CN1 VTEAUZAMSJACBW-UHFFFAOYSA-N 0.000 description 1
- DVKRUSGCEYURRU-UHFFFAOYSA-N n-[3-(1h-imidazol-2-yl)propyl]prop-2-enamide Chemical compound C=CC(=O)NCCCC1=NC=CN1 DVKRUSGCEYURRU-UHFFFAOYSA-N 0.000 description 1
- FMZHDILFTVVEPR-UHFFFAOYSA-N n-[5-(1h-imidazol-2-yl)-2-methyl-5-oxopentan-2-yl]-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(C)(C)CCC(=O)C1=NC=CN1 FMZHDILFTVVEPR-UHFFFAOYSA-N 0.000 description 1
- HLZSKFMYUZLEIH-UHFFFAOYSA-N n-[5-(1h-imidazol-2-yl)-2-methyl-5-oxopentan-2-yl]prop-2-enamide Chemical compound C=CC(=O)NC(C)(C)CCC(=O)C1=NC=CN1 HLZSKFMYUZLEIH-UHFFFAOYSA-N 0.000 description 1
- DVYVMJLSUSGYMH-UHFFFAOYSA-N n-methyl-3-trimethoxysilylpropan-1-amine Chemical compound CNCCC[Si](OC)(OC)OC DVYVMJLSUSGYMH-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000011242 organic-inorganic particle Substances 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- MLBYLEUJXUBIJJ-UHFFFAOYSA-N pent-4-ynoic acid Chemical compound OC(=O)CCC#C MLBYLEUJXUBIJJ-UHFFFAOYSA-N 0.000 description 1
- YZOGOBWHTVNKGA-UHFFFAOYSA-N pentacene-5,7,12,14-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3C(=O)C1=C2 YZOGOBWHTVNKGA-UHFFFAOYSA-N 0.000 description 1
- UFCVADNIXDUEFZ-UHFFFAOYSA-N pentacene-6,13-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC5=CC=CC=C5C=C4C(=O)C3=CC2=C1 UFCVADNIXDUEFZ-UHFFFAOYSA-N 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920005569 poly(vinylidene fluoride-co-hexafluoropropylene) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002954 polymerization reaction product Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920002714 polyornithine Polymers 0.000 description 1
- 108010055896 polyornithine Proteins 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- YOSXAXYCARLZTR-UHFFFAOYSA-N prop-2-enoyl isocyanate Chemical compound C=CC(=O)N=C=O YOSXAXYCARLZTR-UHFFFAOYSA-N 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000006920 protein precipitation Effects 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- DSBYEMVGVLIJFT-UHFFFAOYSA-M sodium 3-(4-benzoylphenoxy)propane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCCOc1ccc(cc1)C(=O)c1ccccc1 DSBYEMVGVLIJFT-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- OIZWHTTYEXZHNB-UHFFFAOYSA-M sodium;carbamimidoyl-[4-[2-(2-methylprop-2-enoyloxy)ethylcarbamoylamino]butyl]azanium;sulfate Chemical compound [Na+].[O-]S([O-])(=O)=O.CC(=C)C(=O)OCCNC(=O)NCCCC[NH2+]C(N)=N OIZWHTTYEXZHNB-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- LZPBKINTWROMEA-UHFFFAOYSA-N tetracene-5,12-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C(=O)C3=CC2=C1 LZPBKINTWROMEA-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- UZNHKBFIBYXPDV-UHFFFAOYSA-N trimethyl-[3-(2-methylprop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)NCCC[N+](C)(C)C UZNHKBFIBYXPDV-UHFFFAOYSA-N 0.000 description 1
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/56—Polyamides, e.g. polyester-amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/78—Graft polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/261—Synthetic macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/264—Synthetic macromolecular compounds derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3206—Organic carriers, supports or substrates
- B01J20/3208—Polymeric carriers, supports or substrates
- B01J20/321—Polymeric carriers, supports or substrates consisting of a polymer obtained by reactions involving only carbon to carbon unsaturated bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3268—Macromolecular compounds
- B01J20/328—Polymers on the carrier being further modified
- B01J20/3282—Crosslinked polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3291—Characterised by the shape of the carrier, the coating or the obtained coated product
- B01J20/3293—Coatings on a core, the core being particle or fiber shaped, e.g. encapsulated particles, coated fibers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3291—Characterised by the shape of the carrier, the coating or the obtained coated product
- B01J20/3297—Coatings in the shape of a sheet
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
- C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/24—Homopolymers or copolymers of amides or imides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
- C09D177/04—Polyamides derived from alpha-amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54393—Improving reaction conditions or stability, e.g. by coating or irradiation of surface, by reduction of non-specific binding, by promotion of specific binding
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/544—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being organic
- G01N33/545—Synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/30—Cross-linking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/38—Graft polymerization
- B01D2323/385—Graft polymerization involving radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/12—Adsorbents being present on the surface of the membranes or in the pores
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/40—Polymers of unsaturated acids or derivatives thereof, e.g. salts, amides, imides, nitriles, anhydrides, esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/022—Preparatory process from polyamines and epihalohydrins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/04—Homopolymers or copolymers of ethene
- C08J2323/06—Polyethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/10—Homopolymers or copolymers of propene
- C08J2323/12—Polypropene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2433/14—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
Definitions
- the present disclosure relates to ligand-functionalized substrates, and methods for preparing the same.
- the functionalized substrates are useful in selectively binding and removing biological materials, such as nucleic acids, host cell proteins, endotoxins, and viruses, from biological samples.
- Detection, quantification, isolation and purification of target biomaterials such as viruses and biomacromolecules (including constituents or products of living cells, for example, proteins, carbohydrates, lipids, and nucleic acids) have long been objectives of investigators. Detection and quantification are important diagnostically, for example, as indicators of various physiological conditions such as diseases. Isolation and purification of biomacromolecules, such as antibodies and enzymes, are important for therapeutic uses and in biomedical research.
- ionic polymers especially cationic polymers, for the flocculation of cell and/or cell debris, as well as for the precipitation of proteins.
- ionic polymers have been used to modify filtration media to enhance the removal of impurities from process streams in depth filtration or membrane adsorber type applications.
- the effectiveness of these polymers is typically reduced as the conductivity of the media being processed increases, i.e. as the salt content increases.
- Chromatographic separation and purification operations can be performed on biological product mixtures, based on the interchange of a solute between a moving phase, which can be a gas or liquid, and a stationary phase. Separation of various solutes of the solution mixture is accomplished because of varying binding interactions of each solute with the stationary phase; stronger binding interactions generally result in longer retention times when subjected to the dissociation or displacement effects of a mobile phase compared to solutes which interact less strongly and, in this fashion, separation and purification can be effected.
- Polymeric resins are widely used for the separation and purification of various target compounds.
- polymeric resins can be used to purify or separate a target compound based on the presence of an ionic group, based on the size of the target compound, based on a hydrophobic interaction, based on an affinity interaction, or based on the formation of a covalent bond.
- polymeric substrates having enhanced affinity for biological materials that allows for selective removal from a biological sample.
- ligand functionalized membranes that overcome limitations in diffusion and binding, and that may be operated at high throughput and at lower pressure drops.
- the present disclosure is directed to ligand-functionalized polymers, methods of making the same, and substrates bearing grafted ligand-functional polymers. More specifically, the substrate comprises grafted thereto a ligand-functionalized polymer and optionally a crosslinked polymer primer layer.
- the ligand group of the ligand-functional polymer comprises guanidinyl monomers, including guanidine and biguanide containing ligands.
- the grafted polymer has the requisite affinity for binding neutral or negatively charged biomaterials, such as cells, cell debris, bacteria, spores, viruses, nucleic acids, endotoxins and proteins, at pH's near or below the pI's of the biomaterials.
- Alkyl means a linear or branched, cyclic or acyclic, saturated monovalent hydrocarbon having from one to about twelve carbon atoms, e.g., methyl, ethyl, 1-propyl, 2-propyl, pentyl, and the like.
- Alkylene means a linear saturated divalent hydrocarbon having from one to about twelve carbon atoms or a branched saturated divalent hydrocarbon having from three to about twelve carbon atoms, e.g., methylene, ethylene, propylene, 2-methylpropylene, pentylene, hexylene, and the like.
- Alkenyl means a linear unsaturated monovalent hydrocarbon having from two to about twelve carbon atoms or a branched unsaturated hydrocarbon having from three to about twelve carbon atoms.
- Aryl means a monovalent aromatic, such as phenyl, naphthyl and the like.
- “Arylene” means a polyvalent, aromatic, such as phenylene, naphthalene, and the like.
- Alkylene means a group defined above with an aryl group attached to the alkylene, e.g., benzyl, 1-naphthylethyl, and the like.
- Heteroarylene refers to a divalent group that is aromatic and heterocyclic. That is, the heteroarylene includes at least one heteroatom in an aromatic ring having 5 or 6 members. Suitable heteroatoms are typically oxy, thio, or amino. The group can have one to five rings that are connected, fused, or a combination thereof. At least one ring is heteroaromatic and any other ring can be aromatic, non-aromatic, heterocyclic, carbocyclic, or a combination thereof. In some embodiments, the heteroarylene has up to 5 rings, up to 4 rings, up to 3 rings, up to 2 rings, or one ring. Examples of heteroarylene groups include, but are not limited to, triazine-diyl, pyridine-diyl, pyrimidine-diyl, pyridazine-diyl, and the like.
- grafted is used throughout to indicate that a covalent chemical bond is formed between the substrate and the ligand-functional polymer.
- hydrocarbyl is inclusive of aryl and alkyl
- Heterohydrocarbyl is inclusive of hydrocarbyl alkyl and aryl groups, and heterohydrocarbyl heteroalkyl and heteroaryl groups, the later comprising one or more catenary (in-chain) heteroatoms such as ether or amino groups.
- Heterohydrocarbyl may optionally contain one or more catenary (in-chain) functional groups including ester, amide, urea, urethane, and carbonate functional groups.
- the non-polymeric (hetero)hydrocarbyl groups typically contain from 1 to 60 carbon atoms.
- heterohydrocarbyls as used herein include, but are not limited to, methoxy, ethoxy, propoxy, 4-diphenylaminobutyl, 2-(2′-phenoxyethoxyl)ethyl, 3,6-dioxaheptyl, 3,6-dioxahexyl-6-phenyl, in addition to those described for “alkyl”, “heteroalkyl”, “aryl”, and “heteroaryl” supra.
- (Hetero)arylene is inclusive of arylene and heteroarylene.
- ligand-functionalized substrates which have enhanced affinity and/or capacity, especially in high ionic strength media, for biological materials, such as host cell proteins, endotoxins, DNA, RNA, viruses, and other microorganisms, at pH's near or below the pI's of the biological materials.
- biological materials such as host cell proteins, endotoxins, DNA, RNA, viruses, and other microorganisms
- the affinity for such biomaterials allows materials that are positively charged at those pH's, such as antibodies, to be purified, as they are not bound to the ligand functional groups.
- the ligand functionalized substrate allows the selective capture or binding of target biomaterials by the ligand groups.
- a ligand functionalized substrate is provided by a) providing a substrate, and b) free-radically grafting the substrate in the presence of a Type II photoinitiator with a guanidinyl functional ligand (meth)acryloyl monomer.
- the substrate may further comprise a primer layer disposed on the surface thereof, the primer layer comprising the reaction product of: 1) a polyamine polymer, 2) a polyfunctional crosslinking agent for the polyamine polymer, and optionally 3) an amine reactive monomer having a polymerizable, ethylenically unsaturated group, preferably a (meth)acryloyl group, and an amine-reactive functional group.
- the guanidinyl functional ligand (meth)acryloyl monomer is grafted to the primer layer in the presence of a Type II photoinitiator.
- the polymer grafted to the surface of the substrate (or primer layer) comprises polymerized ligand-functional monomer units of the formula 1a or b:
- R 1 is H or C 1 -C 4 alkyl
- R 2 is a (hetero)hydrocarbyl group, preferably a divalent alkylene having 1 to 20 carbon atoms
- each R 3 is independently H or hydrocarbyl, preferably C 1 -C 12 alkyl
- R 4 is H, C 1 -C 12 alkyl or —N(R 3 ) 2
- R 5 is H or hydrocarbyl, preferably C 1 -C 12 alkyl or aryl
- X 1 is —O— or —NR 3 —, o is 0 or 1 and n is 1 or 2.
- the grafted polymer comprises 10 to 100 parts by weight of the guanidinyl monomer units, i.e. the grafted (co)polymer may comprise a homopolymer of guanidinyl monomer units.
- Such ligand monomers may be made by condensation of an alkenyl or alkenoyl compound, typically a (meth)acryloyl halide, a (meth)acryloylisocyanate, or an alkenylazlactone, with a compound of formulas 2a or 2b:
- an alkenyl or alkenoyl compound typically a (meth)acryloyl halide, a (meth)acryloylisocyanate, or an alkenylazlactone
- ligand monomers may be made by condensation of a carbonyl containing monomer, such as acrolein, vinylmethylketone, diacetone acrylamide or acetoacetoxyethylmethacrylate, optionally in the presence of a reducing agent, with a compound of formulas 2a or 2b.
- a carbonyl containing monomer such as acrolein, vinylmethylketone, diacetone acrylamide or acetoacetoxyethylmethacrylate
- the ligand-functional alkenyl (co)polymer layer also comprises units derived from a (meth)acryloyl monomer containing at least two free radically polymerizable groups.
- a (meth)acryloyl monomer containing at least two free radically polymerizable groups Such multifunctional (meth)acryloyl monomers, including (meth)acrylate and (meth)acrylamide monomers may be incorporated into the blend of polymerizable monomers to assist in branching or lightly crosslinking of the grafted ligand-functional copolymer.
- Examples of useful multifunctional (meth)acrylates include, but are not limited to, di(meth)acrylates, tri(meth)acrylates, and tetra(meth)acrylates, such as ethyleneglycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, poly(ethylene glycol) di(meth)acrylates, polybutadiene di(meth)acrylate, polyurethane di(meth)acrylates, and propoxylated glycerin tri(meth)acrylate, methylenebisacrylamide, ethylenebisacrylamide, hexamethylenebisacrylamide, diacryloylpiperazine, and mixtures thereof.
- di(meth)acrylates tri(meth)acrylates
- tetra(meth)acrylates such as ethyleneglycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, poly(ethylene glycol) di(meth)acrylates, polybutad
- inclusion of such a multifunctional (meth)acrylate or (meth)acrylamide monomer increases the capacity, particularly the dynamic binding capacity, of the grafted article for capturing biological species.
- Such comonomers are used in amounts of about 0.25 to about 5 parts by weight, preferably of about 1 to about 3 parts by weight, relative to 100 parts total monomer weight. Higher concentrations of polyfunctional comonomer often lead to decreased capacities. While not wanting to be bound by theory, it is believed that this comonomer promotes branching in the grafted (co)polymer layer, thereby leading to increased accessibility or availability of the ligand groups.
- the ligand-functional alkenyl (co)polymer layer may optionally comprise one or more hydrophilic monomers which comprise at least one alkenyl group, preferably a (meth)acryloyl group, and a hydrophilic group, including poly(oxyalkylene) and ionic groups, for providing hydrophilicity to the substrate, or for providing greater selectivity to the substrate when binding biomaterials.
- hydrophilic monomers which comprise at least one alkenyl group, preferably a (meth)acryloyl group, and a hydrophilic group, including poly(oxyalkylene) and ionic groups, for providing hydrophilicity to the substrate, or for providing greater selectivity to the substrate when binding biomaterials.
- the hydrophilic ionic groups may be neutral, have a positive charge, a negative charge, or a combination thereof.
- the ionic group can be neutral or charged depending on the pH conditions. This class of monomers is typically used to impart a desired hydrophilicity to the porous base substrate.
- the addition of a grafting ionic monomer having a positive charge at the selected pH may be used to increase the charge density of the grafted copolymer, allowing increased selectivity of binding or increased capacity of binding for negatively charged contaminants while repelling positively charged biological materials.
- the third monomer may have an acrylate group, or other ethylenically unsaturated groups of reduced reactivity, and a poly(alkylene oxide) group; e.g. monoacrylated poly(alkylene oxide compounds, where the terminus is a hydroxy group or an alkyl ether group.
- the ionic monomers having a negative charge include (meth)acryloylsulfonic acids of Formula 3 or salts thereof.
- Y is a straight or branched alkylene (e.g., an alkylenes having 1 to 10 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms) and L is —O— or —NR 3 —, where R 3 is H or C 1 -C 12 alkyl; R 1 is H or C 1 -C 4 alkyl; and Y is an alkylene (e.g., an alkylene having 1 to 10 carbon atoms, 1 to 6, or 1 to 4 carbon atoms).
- Exemplary ionic monomers according to Formula 3 include, but are not limited to, N-acrylamidomethanesulfonic acid, 2-acrylamidoethanesulfonic acid, 2-acrylamido-2-methyl-1-propanesulfonic acid, and 2-methacrylamido-2-methyl-1-propanesulfonic acid. Salts of these acidic monomers can also be used. Counter ions for the salts can be, for example, ammonium ions, potassium ions, lithium ions, or sodium ions.
- Suitable ionic grafting monomers having a negative charge include sulfonic acids such as vinylsulfonic acid and 4-styrenesulfonic acid; phosphonic acids such as vinylphosphonic acid, (meth)acrylamidoalkylphosphonic acids (e.g., 2-(meth)acrylamidoethylphosphonic acid and 3-(meth)acrylamidopropylphosphonic acid; acrylic acid and methacrylic acid; and carboxyalkyl(meth)acrylates such as 2-carboxyethyl(meth)acrylate, and 3-carboxypropyl(meth)acrylate.
- sulfonic acids such as vinylsulfonic acid and 4-styrenesulfonic acid
- phosphonic acids such as vinylphosphonic acid, (meth)acrylamidoalkylphosphonic acids (e.g., 2-(meth)acrylamidoethylphosphonic acid and 3-(meth)acrylamidopropylphosphonic acid
- Still other suitable acidic monomers include (meth)acryloylamino acids, such as those described in U.S. Pat. No. 4,157,418 (Heilmann).
- Exemplary (meth)acryloylamino acids include, but are not limited to, N-acryloylglycine, N-acryloylaspartic acid, N-acryloyl- ⁇ -alanine, and 2-acrylamidoglycolic acid. Salts of any of these acidic monomers can also be used.
- Some exemplary ionic grafting monomers that are capable of providing a positive charge (at a selected pH) are amino (meth)acrylates or amino (meth)acrylamides of Formula 4 or quaternary ammonium salts thereof.
- the counterions of the quaternary ammonium salts are often halides, sulfates, phosphates, nitrates, and the like.
- L is —O— or —NR 3 —, where R 1 is H or C 1 -C 12 alkyl-; and Y is an alkylene (e.g., an alkylene having 1 to 10 carbon atoms, 1 to 6, or 1 to 4 carbon atoms).
- R 11 is independently hydrogen, alkyl, hydroxyalkyl (i.e., an alkyl substituted with a hydroxy), or aminoalkyl (i.e., an alkyl substituted with an amino).
- the two R 11 groups taken together with the nitrogen atom to which they are attached can form a heterocyclic group that is aromatic, partially unsaturated (i.e., unsaturated but not aromatic), or saturated, wherein the heterocyclic group can optionally be fused to a second ring that is aromatic (e.g., benzene), partially unsaturated (e.g., cyclohexene), or saturated (e.g., cyclohexane).
- aromatic e.g., benzene
- partially unsaturated e.g., cyclohexene
- saturated e.g., cyclohexane
- both R 11 groups are hydrogen.
- one R 11 group is hydrogen and the other is an alkyl having 1 to 10, 1 to 6, or 1 to 4 carbon atoms.
- at least one of R 11 groups is a hydroxy alkyl or an amino alkyl that have 1 to 10, 1 to 6, or 1 to 4 carbon atoms with the hydroxy or amino group being positioned on any of the carbon atoms of the alkyl group.
- the R 11 groups combine with the nitrogen atom to which they are attached to form a heterocyclic group.
- the heterocyclic group includes at least one nitrogen atom and can contain other heteroatoms such as oxygen or sulfur. Exemplary heterocyclic groups include, but are not limited to imidazolyl.
- the heterocyclic group can be fused to an additional ring such as a benzene, cyclohexene, or cyclohexane.
- additional ring such as a benzene, cyclohexene, or cyclohexane.
- exemplary heterocyclic groups fused to an additional ring include, but are not limited to, benzoimidazolyl.
- Exemplary amino acrylates include N,N-dialkylaminoalkyl acrylates such as, for example, N,N-dimethylaminoethylacrylate, N,N-dimethylaminoethylmethacrylate, N,N-diethylaminoethyl acylate, N,N-diethylaminoethylmethacrylate, N,N-dimethylaminopropylacrylate, N,N-dimethylaminopropylmethacrylate, N-tert-butylaminopropylmethacrylate, N-tert-butylaminopropylacrylate and the like.
- N,N-dialkylaminoalkyl acrylates such as, for example, N,N-dimethylaminoethylacrylate, N,N-dimethylaminoethylmethacrylate, N,N-diethylaminoethyl acylate, N,N-die
- Exemplary amino (meth)acrylamides include, for example, N-(3-aminopropyl)methacrylamide, N-(3-aminopropyl)acrylamide, N-[3-(dimethylamino)propyl]methacrylamide, N-(3-imidazolylpropyl)methacrylamide, N-(3-imidazolylpropyl)acrylamide, N-(2-imidazolylethyl)methacrylamide, N-(1,1-dimethyl-3-imidazoylpropyl)methacrylamide, N-(1,1-dimethyl-3-imidazoylpropyl)acrylamide, N-(3-benzoimidazolylpropyl)acrylamide, and N-(3-benzoimidazolylpropyl)methacrylamide.
- Exemplary quaternary salts of the ionic monomers of Formula 4 include, but are not limited to, (meth)acrylamidoalkyltrimethylammonium salts (e.g., 3-methacrylamidopropyltrimethylammonium chloride and 3-acrylamidopropyltrimethylammonium chloride) and (meth)acryloxyalkyltrimethylammonium salts (e.g., 2-acryloxyethyltrimethylammonium chloride, 2-methacryloxyethyltrimethylammonium chloride, 3-methacryloxy-2-hydroxypropyltrimethylammonium chloride, 3-acryloxy-2-hydroxypropyltrimethylammonium chloride, and 2-acryloxyethyltrimethylammonium methyl sulfate).
- (meth)acrylamidoalkyltrimethylammonium salts e.g., 3-methacrylamidopropyltrimethylammonium chloride and 3-acrylamidopropyltrimethylammonium chlor
- Neutral hydrophilic monomers that may be incorporated are poly(alkylene oxide) monomers having a (meth)acryloyl or non-acryloyl ethylenically unsaturated group and a non-polymerizable terminus.
- Such monomers may be of the formula 5: CH 2 ⁇ CR 1 —C(O)—X 1 —(CH(R 1 )—CH 2 —O) n —R 1 , 5 wherein each R 1 is independently H or C 1 -C 4 alkyl, X 1 is —O— or —NR 3 —, where R 3 is H or C 1 -C 12 alkyl and n is 2 to 100.
- alkenylazlactones adducts of polyetheramines such as the monoamine, diamine and triamines based on the polyetheramine structure.
- polyetheramines such as the monoamine, diamine and triamines based on the polyetheramine structure.
- Jeffamine® series is the Jeffamine® series, from Huntsman, The Woodlands, Tex., USA.
- Other useful neutral, hydrophilic comonomers include dimethylacrylamide, acrylamide, methacrylamide, hydroxyethyl(meth)acrylate, hydroxypropyl(meth)acrylate, N-vinylpyrrolidinone, or combinations thereof.
- Such optional hydrophilic comonomers are used in amounts of about 0 to 90 parts by weight, 1 to about 90 parts by weight, preferably of about 5 to about 50 parts by weight, relative to 100 parts total monomer weight.
- the hydrophilic monomer is an anionic monomer, it is used in amounts of 15 parts be weight or less, so as to not reduce the ability of the grafted substrate to interact with and capture negatively charged biological materials.
- the substrate is provided with a grafted polymer of the formula 10: -(M Lig ) y -(M Hydrophil ) x -(M crosslink ) z -, 6 where (M Lig ) y are guanidinyl ligand functional monomer units having “y” polymerized monomer units, (M Hydrophil ) x are hydrophilic monomer units having “x” polymerized monomer units, (M crosslink ) are multifunctional (meth)acrylate monomer units having “z” polymerized monomer units, y is 10 to 100 parts by weight of the (M Lig ) monomer units; x is 0 to 90 parts by weight of the (M hydrophil ) monomer units; z is 0 to 5 parts by weight of the (M Crosslink ) monomer units, where the total is 100 parts by weight.
- the monomer units are simplified for clarity and monomers other than the depicted M lig monomer may be covalently bonded with the substrate. It is believed that the multifunctional acrylate will crosslink the grafted ligand functional polymer, and/or will further provide grafted hyperbranched polymers with ligand functional groups. It is further believed that minor amounts of free, ungrafted polymer may be present on the surface of the substrate, which may further be crosslinked and/or hyperbranched to the extent that it is physically entangled with the grafted copolymer.
- the substrate may be in any form such as particles, fibers, films or sheets. Suitable particles include, but are not limited to, organic particles, inorganic particles, and porous and nonporous particles.
- the base substrate is porous. Suitable porous base substrates include, but are not limited to, porous particles, porous membranes, porous nonwoven webs, and porous fibers
- the substrate may be formed from any suitable thermoplastic polymeric material.
- suitable polymeric materials include, but are not limited to, polyolefins, poly(isoprenes), poly(butadienes), fluorinated polymers, chlorinated polymers, polyamides, polyimides, polyethers, poly(ether sulfones), poly(sulfones), poly(vinyl acetates), polyesters such as poly(lactic acid), copolymers of vinyl acetate, such as poly(ethylene)-co-poly(vinyl alcohol), poly(phosphazenes), poly(vinyl esters), poly(vinyl ethers), poly(vinyl alcohols), and poly(carbonates).
- the thermoplastic polymer may be surface treated, such as by plasma discharge, to provide suitable functionality to the surface of the substrate.
- Surface treatment provides functional groups such as hydroxyl groups that can improve wetting by the coating or optional primer solution.
- One such useful plasma treatment is described in U.S. Pat. No. 7,125,603 (David et al.).
- Suitable polyolefins include, but are not limited to, poly(ethylene), poly(propylene), poly(l-butene), copolymers of ethylene and propylene, alpha olefin copolymers (such as copolymers of ethylene or propylene with 1-butene, 1-hexene, 1-octene, and 1-decene), poly(ethylene-co-1-butene) and poly(ethylene-co-1-butene-co-1-hexene).
- Suitable fluorinated polymers include, but are not limited to, poly(vinyl fluoride), poly(vinylidene fluoride), copolymers of vinylidene fluoride (such as poly(vinylidene fluoride-co-hexafluoropropylene), and copolymers of chlorotrifluoroethylene (such as poly(ethylene-co-chlorotrifluoroethylene).
- Suitable polyamides include, but are not limited to, poly(iminoadipolyliminohexamethylene), poly(iminoadipolyliminodecamethylene), and polycaprolactam.
- Suitable polyimides include, but are not limited to, poly(pyromellitimide).
- Suitable poly(ether sulfones) include, but are not limited to, poly(diphenylether sulfone) and poly(diphenylsulfone-co-diphenylene oxide sulfone).
- Suitable copolymers of vinyl acetate include, but are not limited to, poly(ethylene-co-vinyl acetate) and such copolymers in which at least some of the acetate groups have been hydrolyzed to afford various poly(vinyl alcohols).
- a preferred substrate is a porous substrate that is a microporous membrane such as a solvent-induced phase separation (SIPS) membrane.
- the porous base substrate comprises a nylon microporous film or sheet, such as those described in U.S. Pat. No. 6,056,529 (Meyering et al.), U.S. Pat. No. 6,267,916 (Meyering et al.), U.S. Pat. No. 6,413,070 (Meyering et al.), U.S. Pat. No. 6,776,940 (Meyering et al.), U.S. Pat. No. 3,876,738 (Marinacchio et al.), U.S. Pat. No. 3,928,517, U.S. Pat. No. 4,707,265 (Knight et al.), and U.S. Pat. No. 5,458,782 (Hou et al.).
- the porous substrate is a thermally-induced phase separation (TIPS) membrane.
- TIPS thermally-induced phase separation
- These are often prepared by forming a solution of a thermoplastic material and a second material above the melting point of the thermoplastic material. Upon cooling, the thermoplastic material crystallizes and phase separates from the second material. The crystallized material is often stretched. The second material is optionally removed either before or after stretching.
- Microporous membranes are further disclosed in U.S. Pat. No. 4,529,256 (Shipman); U.S. Pat. No. 4,726,989 (Mrozinski); U.S. Pat. No. 4,867,881 (Kinzer); U.S. Pat. No. 5,120,594 (Mrozinski); U.S. Pat. No.
- TIPS membranes comprise poly(vinylidene fluoride) (PVDF), polyolefins such as poly(ethylene) or poly(propylene), vinyl-containing polymers or copolymers such as ethylene-vinyl alcohol copolymers and butadiene-containing polymers or copolymers, and acrylate-containing polymers or copolymers.
- PVDF poly(vinylidene fluoride)
- polyolefins such as poly(ethylene) or poly(propylene)
- vinyl-containing polymers or copolymers such as ethylene-vinyl alcohol copolymers and butadiene-containing polymers or copolymers
- acrylate-containing polymers or copolymers for some applications, a TIPS membrane comprising PVDF is particularly desirable. TIPS membranes comprising PVDF are further described in U.S. Pat. No. 7,338,692 (Smith et al.).
- the substrate may be in any form such as films or sheets.
- the base substrate is porous.
- Suitable porous base substrates include, but are not limited to, porous membranes, porous woven and nonwoven webs, and porous fibers.
- the base substrate has an average pore size that is typically greater than about 0.2 micrometers in order to minimize size exclusion separations, minimize diffusion constraints and maximize surface area and separation based on binding of a target molecule.
- the pore size is in the range of 0.1 to 10 micrometers, preferably 0.5 to 3 micrometers and most preferably 0.8 to 2 micrometers when used for binding of biological materials. The efficiency of binding other target molecules may confer different optimal ranges.
- the porous base substrate is a nonwoven web which may include nonwoven webs manufactured by any of the commonly known processes for producing nonwoven webs.
- nonwoven web refers to a fabric that has a structure of individual fibers or filaments which are randomly and/or unidirectionally interlaid in a mat-like fashion.
- the fibrous nonwoven web can be made by wet laid, carded, air laid, spunlaced, spunbonding or melt-blowing techniques or combinations thereof.
- Spunbonded fibers are typically small diameter fibers that are formed by extruding molten thermoplastic polymer as filaments from a plurality of fine, usually circular capillaries of a spinneret with the diameter of the extruded fibers being rapidly reduced.
- Meltblown fibers are typically formed by extruding the molten thermoplastic material through a plurality of fine, usually circular, die capillaries as molten threads or filaments into a high velocity, usually heated gas (e.g. air) stream which attenuates the filaments of molten thermoplastic material to reduce their diameter.
- heated gas e.g. air
- meltblown fibers are carried by the high velocity gas stream and are deposited on a collecting surface to from a web of randomly dispersed meltblown fibers.
- Any of the non-woven webs may be made from a single type of fiber or two or more fibers that differ in the type of thermoplastic polymer and/or thickness.
- the substrate optionally has a primer layer disposed on the substrate comprising the reaction product of: 1) a polyamine polymer, 2) a polyfunctional crosslinking agent for the polyamine polymer, and 3) an amine reactive monomer having a polymerizable, ethylenically unsaturated group, preferably a (meth)acryloyl group, and an amine-reactive functional group; and c) a ligand-functional alkenyl (co)polymer layer grafted to the primer layer.
- the primer layer is coated on the substrate and cured to form a durable, crosslinked polyamine polymer layer having polymerizable, ethylenically unsaturated groups, preferably (meth)acryloyl groups, on the surface thereof.
- the crosslinking of the polyamine polymer is effected by the 2) polyfunctional crosslinking agent, which has two or more amine-reactive functional groups, such as epoxy groups.
- the crosslinked polyamine polymer is simultaneously or sequentially functionalized with primer component 3), having an amine-reactive group for coupling (by forming a covalent bond) to the crosslinked polyamine polymer, and an ethylenically unsaturated group, such as a (meth)acryloyl group, which may be used to free-radically graft the c) ligand-functional alkenyl (co)polymer layer to the crosslinked polyamine polymer layer.
- the primer base polymer comprises a polyamine polymer; i.e. a polymer having primary or secondary amino groups that may be pendant or catenary, i.e. in the polymer chain.
- the aminopolymers contain primary or secondary amine groups and can be prepared by chain growth or step growth polymerization procedures with the corresponding monomers. These monomers can also, if desired, be copolymerized with other monomers.
- the polymer can also be a synthesized or naturally occurring biopolymer. If any of these polymers, irrespective of source, do not contain primary or secondary amine groups, these functional groups can be added by the appropriate chemistry.
- Useful aminopolymers are water soluble or water-dispersible.
- water soluble refers to a material that can be dissolved in water. The solubility is typically at least about 1 milligram, preferably 5 milligram, more preferably 10 milligram, per milliliter of water.
- water dispersible refers to a material that is not water soluble but that can be emulsified or suspended in water. In some embodiments mixed aqueous/alcoholic solvent systems may be advantageous.
- aminopolymers suitable for use which are prepared by chain growth polymerization include, but are not limited to: polyvinylamine, poly(N-methylvinylamine), polyethylenimine, polypropylenimine, polyallylamine, polyallylmethylamine, polydiallylamine, poly(4-aminomethylstyrene), poly(4-aminostyrene), poly(acrylamide-co-methylaminopropylacrylamide), and poly(acrylamide-co-aminoethylmethacrylate).
- amino polymers suitable for use include, but are not limited to: polyethylenimine, polypropylenimine, polylysine, polyornithine, polyaminoamides, polydimethylamine-epichlorohydrin-ethylenediamine, and certain polyaminosiloxanes, which can be built from monomers such as aminopropyltriethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-trimethoxysilylpropyl-N-methylamine, and bis(trimethoxysilylpropyl)amine.
- Useful aminopolymers may also include those that have primary or secondary amino end groups and include, but are not limited to, those formed from polyamidoamine (PAMAM) and polypropylenimine: e.g. DAB-Am and PAMAM dendrimers (or hyperbranched polymers containing the amine functional group).
- PAMAM polyamidoamine
- DAB-Am polypropylenimine
- PAMAM dendrimers or hyperbranched polymers containing the amine functional group.
- Dendrimeric material formed from PAMAM are commercially available under the trade designation StarburstTM (PAMAM) dendrimer (e.g., Generation 0 with 4 primary amino groups, Generation 1 with 8 primary amino groups, Generation 2 with 16 primary amino groups, Generation 3 with 32 primary amino groups, and Generation 4 with 64 primary amino groups) from Aldrich Chemical, Milwaukee, Wis.
- Dendrimeric material formed from polypropylenimine is commercially available under the trade designation “DAB-AM” from Aldrich Chemical.
- DAB-Am-4 is a generation 1 polypropylenimine tetraamine dendrimer with 4 primary amino groups
- DAB-Am-8 is a generation 2 polypropylenimine octaamine dendrimer with 8 primary amino groups
- DAB-Am-16 is a generation 3 polypropylenimine hexadecaamine with 16 primary amino groups
- DAB-Am-32 is a generation 4 polypropylenimine dotriacontaamine dendrimer with 32 primary amino groups
- DAB-Am-64 is a generation 5 polypropylenimine tetrahexacontaamine dendrimer with 64 primary amino groups.
- aminopolymers suitable for use which are biopolymers include chitosan, glucosamine- and galactosamine-containing polysaccharides, and starch, where the latter is reacted with reagents such as methylaminoethylchloride.
- aminopolymers suitable for use include polyacrylamide homo- or copolymers with amino monomers including aminoalkyl(meth)acrylate, (meth)acrylamidoalkylamine, and diallylamine.
- Preferred aminopolymers include polyamidoamines, polyethyleneimine, polyvinylamine, polyallylamine, and polydiallylamine.
- Suitable commercially available aminopolymers include, but are not limited to, polyamidoamines such as ANQUAMINETM 360, 401, 419, 456, and 701 (Air Products and Chemicals, Allentown, Pa.); LUPASOLTM polyethylenimine polymers such as FG, PR 8515, Waterfree, P, PS (BASF Corporation, Rensselaer, N.Y.); polyethylenimine polymers such as CORCATTM P-600 (EIT Company, Lake Wylie, S.C.); and polyamide resins such as the VERSAMID series of resins that are formed by reacting a dimerized unsaturated fatty acid with polyalkylene polyamines (Cognis Corporation, Cincinnati, Ohio).
- polyamidoamines such as ANQUAMINETM 360, 401, 419, 456, and 701 (Air Products and Chemicals, Allentown, Pa.)
- LUPASOLTM polyethylenimine polymers such as FG, PR 8515, Waterfree, P, PS
- the primer layer has a crosslinking agent for the polyamine polymer having at least two amine-reactive functional groups, including ketone, aldehyde, ester, acyl halide, isocyanate, epoxide, anhydride, or azlactone groups.
- amine-reactive functional groups Z are selected to react with the amine groups of the polyamine polymer at temperatures below about 50° C., preferably below 25° C. such that the crosslinking reaction takes place during the coating and drying operation.
- Preferable crosslinking agents are further water-soluble or water-dispersible.
- Such crosslinking agents may have the general formula 1: R 8 —(Z) y , 7 where R 8 is a (hetero)hydrocarbyl group, Z is an amine-reactive group and y is ⁇ 2, preferably 2-4.
- the R 8 group may be an alkylene group, an arylene group, a heteroarylene group, a heteroalkylene group, an aralkylene group, or a combination thereof.
- the amine-reactive Z group may be an epoxy group and include both aliphatic and aromatic polyepoxides.
- Representative examples of aliphatic polyepoxides include 3′,4′-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxycyclohexyloxirane, 2-(3′,4′-epoxycyclohexyl)-5,1′′-spiro-3′′,4′′-epoxycyclohexane-1,3-dioxane, bis(3,4-epoxycyclohexylmethyl)adipate, the diglycidyl ester of linoleic dimer acid, 1,4-bis(2,3-epoxypropoxy)butane, 4-(1,2-epoxyethyl)-1,2-epoxycyclohexane, 2,2-bis(3,4-epoxycyclohexyl)propane, polyglycid
- aromatic polyepoxides which can be utilized in the composition of the invention include glycidyl esters of aromatic carboxylic acids, e.g., phthalic acid diglycidyl ester, isophthalic acid diglycidyl ester, trimellitic acid triglycidyl ester, and pyromellitic acid tetraglycidyl ester, and mixtures thereof; N-glycidylaminobenzenes, e.g., N,N-diglycidylbenzeneamine, bis(N,N-diglycidyl-4-aminophenyl)methane, 1,3-bis(N,N-diglycidylamino)benzene, and N,N-diglycidyl-4-glycidyloxybenzeneamine, and mixtures thereof; and the polyglycidyl derivatives of polyhydric phenols, e.g., 2,2-bis-[4-(2,3-epoxypropoxyl)phenyl
- the amine reactive functional group Z may be an isocyanate group.
- Suitable polyisocyanates include organic compounds containing at least two free isocyanate groups.
- Diisocyanates of the formula R 8 (NCO) 2 are preferably used wherein R 8 denotes an aliphatic hydrocarbon group with 4 to 20 carbon atoms, a cycloaliphatic hydrocarbon group with 6 to 20 carbon atoms, an aromatic hydrocarbon group with 6 to 20 carbon atoms or an araliphatic hydrocarbon group with 7 to 20 carbon atoms.
- diisocyanates examples include tetramethylene diisocyanate, hexamethylenediisocyanate (HDI), dodecamethylenediisocyanate, 1,4-diisocyanatocyclohexane, 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexane (IPDI), 4,4′-diisocyanato-dicyclohexylmethane (HMDI), 4,4′-diisocyanato-2,2-dicyclohexyl-propane, 1,4-diisocyanatobenzene, 2,4-diisocyanatotoluene (TDI), 2,6-diisocyanatotoluene, 4,4′-diisocyanatodiphenylmethane (MDI), m- and p-xylylenediisocyanate, ⁇ , ⁇ , ⁇ ′, ⁇ ′-tetramethyl-m-
- the amine reactive functional group Z may be an azlactone group.
- azlactone group Reference may be made to Table 1 of a review entitled “Polyazlactones” by J. K. Rasmussen, et al., Encyclopedia of Polymer Science and Engineering, Second Edition, Volume 11, 1988, pp. 558-571 that contains a listing of reported bis(azlactones).
- Other poly azlactone functional materials are described in U.S. Pat. No. 7,556,858 (Rasmussen et al.), incorporated herein by reference.
- the amine reactive functional group Z may be an aldehyde or ketone group.
- aldehyde or ketone group examples include bis- and polyaldehydes, such as glyoxal or glutaraldehyde.
- the crosslinking agent may be a polyacyl compound where Z is an ester, acid, acid halide or anhydride group.
- Esters and acids are less preferred due to the reduced reactivity.
- suitable diacyl compounds as the corresponding esters, halides, acids, and anhydrides: azelaic; maleic; fumaric; itaconic; 1,5-pent-2-enedioic; adipic; 2-methyleneadipic; 3-methylitaconic; 3,3-dimethylitaconic; sebacic; suberic; pimelic; succinic; benzylsuccinic; sulfosuccinic; glutaric; 2-methyleneglutaric; 2-sulfoglutaric; 3-sulfoglutaric; diglycolic; dilactic; 3,3′-(ethylenedioxy)dipropionic; dodecanedioic; 2-sulfododecanedioic; decanedio
- the crosslinking agent for the polyamine polymer may be provided in an amount wherein the number of equivalents of amine reactive groups Z is at least 2%, preferably at least 5%, and up to about 20%, relative to the number of equivalents of amine groups in the polyamine polymer.
- the primer layer optionally further comprises an amine reactive monomer having a polymerizable, ethylenically unsaturated group and an amine-reactive functional group, some embodiments of which are of the formula 8:
- X 1 is —O— or —NR 3 —, where R 3 is H or C 1 -C 12 alkyl, R 1 is H or C 1 -C 4 alkyl; R 7 is a single bond or a (hetero)hydrocarbyl linking group, A is a functional group that is reactive with the amino groups of the polyamine polymer, and x is 0 or 1.
- compounds of Formula 8 are (meth)acryloyl compounds, and in other embodiments are alkenyl compounds.
- R 7 is a single bond or a hydrocarbyl linking group that joins an ethylenically unsaturated, polymerizable group (e.g. alkenyl or (meth)acryl group) to reactive functional group A and preferably is an alkylene group having 1 to 6 carbon atoms, a 5- or 6-membered cycloalkylene group having 5 to 10 carbon atoms, or a divalent aromatic group having 6 to 16 carbon atoms; and A is a reactive functional group capable of reacting with an amine group of the polyamine polymer for the incorporation of a free-radically polymerizable group.
- ethylenically unsaturated, polymerizable group e.g. alkenyl or (meth)acryl group
- reactive functional group A preferably is an alkylene group having 1 to 6 carbon atoms, a 5- or 6-membered cycloalkylene group having 5 to 10 carbon atoms, or a divalent aromatic group having 6 to 16 carbon atoms
- A
- Useful reactive functional groups “A” include carboxyl, oxazolinyl, azlactone, acetyl, acetonyl, acetoacetyl, ester, isocyanato, epoxy, aziridinyl, acyl halide, and cyclic anhydride groups.
- the amine-reactive functional groups A are selected to react with the amine groups of the polyamine polymer at temperatures below about 50° C., preferably below 25° C. such that the reaction takes place during the coating and drying operation.
- Preferable amine reactive monomers are further water-soluble or water-dispersible.
- Representative azlactone group-substituted functional compounds of Formula 2 include: 2-ethenyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-1,3-oxazolin-5-one; 2-isopropenyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-1,3-oxazolin-5-one; 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one; 2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-4-ethyl-1,3-oxazolin-5-one; 2-isopropenyl-3-oxa-1-aza[4.5]spirodec-1-ene-4-one; 2-ethenyl-5,6-dihydro-4H-1,3-oxazin-6-one; 2-ethenyl-4,5,6,7
- Representative acetoacetyl group-substituted functional compounds of Formula 8 include 2-(acetoacetoxy)ethyl methacrylate.
- Representative carboxyl group-substituted functional compounds of Formula 8 include (meth)acrylic acid, 3-(meth)acryloyloxy-propionic acid, 4-(meth)acryloyloxy-butyric acid, 2-(meth)acryloyloxy-benzoic acid, 3-(meth)acryloyloxy-5-methyl benzoic acid, 4-(meth)acryloyloxymethyl-benzoic acid, phthalic acid mono-[2-(meth)acryloyloxy-ethyl]ester, 2-butynoic acid, and 4-pentynoic acid.
- Representative isocyanate group-substituted functional compounds of Formula 8 include 2-isocyanatoethyl (meth)acrylate, 3-isocyanatopropyl (meth)acrylate, 4-isocyanatocyclohexyl (meth)acrylate, 4-isocyanatostyrene, 2-methyl-2-propenoyl isocyanate, 4-(2-(meth)acryloyloxyethoxycarbonylamino) phenylisocyanate, allyl 2-isocyanatoethylether, and 3-isocyanato-1-propene.
- Representative epoxy group-substituted functional compounds of Formula 8 include glycidyl (meth)acrylate, thioglycidyl (meth)acrylate, 3-(2,3-epoxypropoxy)phenyl (meth)acrylate, 2-[4-(2,3-epoxypropoxyl)phenyl]-2-(4-(meth)acryloyloxy-phenyl)propane, 4-(2,3-epoxypropoxyl)cyclohexyl (meth)acrylate, 2,3-epoxycyclohexyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate.
- Representative acyl halide group-substituted functional compounds of Formula 8 include (meth)acryloyl chloride, ⁇ -chloro(meth)acryloyl chloride, (meth)acryloyloxyacetyl chloride, 5-hexenoyl chloride, 2-(acryloyloxy) propionyl chloride, 3-(acryloylthioxy) propionoyl chloride, and 3-(N-acryloyl-N-methylamino) propionoyl chloride.
- amine-reactive monomers include anhydride group-substituted functional monomers including maleic anhydride, (meth)acrylic anhydride, itaconic anhydride, 3-(meth)acryloyloxyphthalic anhydride, and 2-(meth)acryloxycyclohexanedicarboxylic acid anhydride.
- the ligand-functionalized monomer is graft (co)polymerized onto the substrate, which may be primed or unprimed.
- the substrate is coated with an imbibing solution comprising the ligand-functionalized monomer, any comonomers, a Type II photoinitiator, and a solvent for the mixture.
- the Type II photoinitiator is used in an amount effective to facilitate hydrogen abstraction from the surface of the substrate to provide an incipient free radical, and free radical addition of the monomer(s) to produce the grafted (co)polymer.
- the photoinitiators can be used in amounts from about 0.001 part by weight to about 15 parts, preferably from about 0.5 to about 5 parts, by weight based on 100 parts total monomer.
- the method further comprises a radiation-sensitive hydrogen abstracting photoinitiator having the general formula: Ar—CO—R 13 9 in which Ar is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms optionally substituted with a C 1 to C 12 alkyl group, a C 1 to C 12 alkoxy group, or a phenyl group; and R 13 is a C 1 to C 6 alkyl group, a cycloalkyl group having 3 to 14 carbon atoms, or Ar
- Included among those hydrogen abstracting photoinitiators encompassed by Formula 9 include benzophenone, 4-(3-sulfopropyloxyl)benzophenone sodium salt, Michler's ketone, benzil, anthraquinone, 5,12-naphthacenequinone, aceanthracenequinone, benz(A)anthracene-7,12-dione, 1,4-chrysenequinone, 6,13-pentacenequinone, 5,7,12,14-pentacenetetrone, 9-fluorenone, anthrone, xanthone, thioxanthone, 2-(3-sulfopropyloxyl)thioxanthen-9-one, acridone, dibenzosuberone, acetophenone, and chromone.
- the above-described ligand functionalized substrates may be prepared using a combination of process steps.
- the method comprises:
- the solvent for the imbibing solution may be any polar solvent.
- the solvent is water or a water/water-miscible organic solvent mixture.
- the ratio of water to organic solvent can vary widely, depending upon monomer solubility. With some monomers, it is typically greater than 1:1 (v/v) water to organic solvent, preferably greater than 5:1, and more preferably greater than 7:1. With other monomers, a higher proportion of organic solvent, even up to 100%, with some alcohols especially, may be preferred.
- any such water miscible organic solvent preferably has no groups that would retard the polymerization.
- the water miscible solvents are protic group containing organic liquids such as the lower alcohols having 1 to 4 carbon atoms, lower glycols having 2 to 6 carbon atoms, and lower glycol ethers having 3 to 6 carbon atoms and 1 to 2 ether linkages.
- higher glycols such as poly(ethylene glycol) may be used.
- methanol ethanol
- isopropanol n-butanol
- t-butyl alcohol ethylene glycol
- methoxyethanol ethoxyethanol
- propoxyethanol butoxyethanol
- methyl carbitol ethyl carbitol
- mixtures thereof methyl carbitol, ethyl carbitol, and mixtures thereof.
- non-protic water miscible organic solvents that can also be used such as aliphatic esters and ketones and sulfoxides methoxyethyl acetate, ethoxyethyl acetate, propoxyethyl acetate, butoxyethyl acetate, triethyl phosphate, acetone, methyl ethyl ketone, methyl propyl ketone and dimethyl sulfoxide.
- the concentration of each component in the imbibing solution may vary depending on a number of factors including, but not limited to, the grafting monomer or monomers in the imbibing solution, the extent of grafting desired, the reactivity of the grafting monomer(s), and the solvent used.
- the total concentration of the monomers in the imbibing solution ranges from about 0.1 wt % to about 60 wt %, desirably, from about 1 wt % to about 35 wt %, more desirably, from about 5% to about 25%, based on a total weight of the imbibing solution.
- typical total weight gains by the substrate are in the range of about 5% to about 30%, in the range of about 10% to about 25%, or in the range of about 12% to about 20%.
- UV light sources can be relatively low light intensity sources such as blacklights which provide generally 10 mW/cm 2 or less (as measured in accordance with procedures approved by the United States National Institute of Standards and Technology as, for example, with a UVIMAPTM UM 365 L-S radiometer manufactured by Electronic Instrumentation & Technology, Inc., in Sterling, Va.) over a wavelength range of 280 to 400 nanometers, or relatively high light intensity sources such as medium pressure mercury lamps which provide intensities generally greater than 10 mW/cm 2 , preferably between 15 and 450 mW/cm 2 . Where UV radiation is used to fully or partially polymerize the composition, moderate intensities and longer exposure times are preferred.
- blacklights which provide generally 10 mW/cm 2 or less (as measured in accordance with procedures approved by the United States National Institute of Standards and Technology as, for example, with a UVIMAPTM UM 365 L-S radiometer manufactured by Electronic Instrumentation & Technology, Inc., in Sterling, Va.) over a wavelength range of
- an intensity of about 10 to 50 mW/cm 2 and an exposure time of about 1 to 5 seconds may be used successfully.
- an exposure time of up to about 30 minutes may be used.
- a preferred UV source is the Quant 48TM UV Curing System from Quantum Technologies, Irvine, Calif.
- the grafted substrate may be subjected to an optional washing/rinsing step, where the functionalized substrate is washed or rinsed one or more times in a rinse chamber to remove any unreacted monomers, solvent or other reaction by-products from the functionalized substrate.
- the functionalized substrate is washed or rinsed up to four times using a water rinse, a saline rinse, and optionally an alcohol rinse, a combination of water and alcohol rinses, and/or a solvent rinse (e.g., acetone, MEK, etc).
- a solvent rinse e.g., acetone, MEK, etc.
- the rinse may include one or more alcohols including, but not limited to, isopropanol, methanol, ethanol, or any other alcohol that is practical to use and an effective solvent for any residual monomer.
- the functionalized substrate may pass through a rinse bath or a rinse spray.
- the functionalized substrate is dried to remove any rinse solvent from the functionalized substrate.
- the functionalized substrate is dried in an oven having a relatively low oven temperature for a desired period of time (referred to herein as “oven dwell time”).
- Oven temperatures typically range from about 30° C. to about 120° C.
- oven dwell times typically range from about 120 to about 600 seconds.
- Any conventional oven may be used in the optional drying step. Suitable ovens include, but are not limited to, convection ovens and recirculating air ovens.
- any of the above-mentioned porous base substrates, grafting monomers, and reactants may be used to form a given functionalized substrate.
- the porous base substrate is often in the form of a porous membrane such as a microporous membrane, a nonwoven web, or porous fibers.
- the porous base substrate comprises a microporous membrane formed by a solvent-induced phase separation (SIPS) method.
- SIPS solvent-induced phase separation
- the methods provide an article having a ligand functionalized coating covalently grafted on the surface thereof, the ligand functionalized coating comprising the UV polymerization reaction product of a one or more ligand monomers, one or more ethylenically unsaturated crosslinking monomers and one or more hydrophilic monomers, the free radical polymerization product being the result of hydrogen abstraction from the surface of the substrate.
- the method of making a ligand functionalized substrate alters the original nature of the porous base substrate, as the grafted and UV polymerized species include a ligand group.
- the method enables the formation of ligand functionalized substrates having many of the advantages of a porous bases substrate (e.g., mechanical and thermal stability, porosity), but with enhanced affinity for biomolecules such as nucleic acids, host cell proteins, endotoxins, and microbes, resulting from the monomers and steps used to form a given functionalized substrate.
- the porous substrates having a coating of ligand-functionalized polymer are particularly suited as filter media, for the selective binding and removal of target biological species including proteins, cells, cell debris, microbes, nucleic acids, and/or viruses from biological samples.
- target biological species including proteins, cells, cell debris, microbes, nucleic acids, and/or viruses from biological samples.
- the present disclosure further provides a method for the removal of target biological species from a biological sample by contacting the sample with the ligand polymer functionalized substrate as described herein.
- target biological species may include a contaminant or a species of interest.
- the ligand functionalized substrate is useful for the purification of biological or other fluid samples comprising biologically derived species (biological species).
- biological species include, but are not limited to, cells, cell debris, proteins, nucleic acids, endotoxins, and viruses.
- the biological species being removed from the fluid is the object of the purification.
- a recombinant protein or enzyme may be prepared in cell culture or by fermentation, and the substrate can be used to capture the protein or enzyme as the first step in the purification process.
- the substrate may be used to capture microorganisms from a fluid as the first step in a process of concentrating, enumerating, and/or identifying the microorganisms.
- the biological species being removed from the fluid is a contaminant that must be removed prior to additional processing steps for the fluid.
- the ligand functional substrates are useful under conditions of high salt concentration or high ionic strength, i.e., they are “salt tolerant”.
- salt is meant to include all low molecular weight ionic species which contribute to the conductivity of the solution.
- the importance of utility of the ligand functional substrates in the presence of salt is that many process solutions used in biopharmaceutical or enzyme manufacture have conductivities in the range of 15-30 mS/cm (approximately 150-300 mM salt) or more. Salt tolerance can be measured in comparison to that of the conventional quaternary amine or Q ligand (e.g.
- trimethylammonium ligand whose primarily electrostatic interactions with many biological species rapidly deteriorates at conductivities three- to six-fold less than the target range of 15-30 mS/cm.
- the process fluid may have to be diluted two-fold or more in order to reduce the conductivity to an acceptable range. This is expensive and dramatically increases the overall processing time.
- ligand functionalized substrates in which the ligands comprise guanidine or biguanide groups perform extremely well under high ionic strength conditions.
- the biological sample is contacted with the ligand functionalized substrate for a time sufficient to interact and form a complex with the target biological species disposed (dissolved or suspended) in the solution when the solution comprises from 0 to about 50 mM salt, preferably when the solution comprises from 0 to about 150 mM salt, more preferably when the solution comprises from 0 to about 300 mM salt or higher, such that the concentration of the target biological species remaining disposed in the solution is less than 50% of its original concentration.
- the solution is contacted with the ligand functionalized substrate for a time sufficient to interact and form a complex with the target biological species disposed in the solution when the solution comprises from 0 to about 50 mM salt, preferably when the solution comprises from 0 to about 150 mM salt, more preferably when the solution comprises from 0 to about 300 mM salt or higher, such that the concentration of the target biological species remaining disposed in the solution is less than 10% of its original concentration.
- the solution is contacted with the ligand functionalized substrate for a time sufficient to interact and form a complex with the target biological species disposed in the solution when the solution comprises from 0 to about 50 mM salt, preferably when the solution comprises from 0 to about 150 mM salt, more preferably when the solution comprises from 0 to about 300 mM salt or higher, such that the concentration of the target biological species remaining disposed in the solution is less than 1% of its original concentration.
- the substrate may be functionalized so that other proteins are excluded or repelled from the ligand functionalized substrate, while negatively charged biological species bind to the ligand functional groups of Formulas Ia and Ib.
- negatively charged biological species bind tenaciously to the ligand functional group of Formulas Ia and Ib. This finding is particularly advantageous when the target biological species is a contaminant and the ligand functionalized substrate is part of a disposable filtration or purification device.
- the target biological species is the object of isolation or purification, it is important to be able to elute the captured species from the functionalized substrate.
- the strength of the interaction with the ligand functionalized substrate may be reduced by lowering the amount of monomer of Formula 1a or 1b in the grafted copolymer.
- the substrate may be grafted with one or more ionic comonomers.
- the porous substrate may comprise grafted ionic groups that are positively charged at the selected pH of the biological sample solution to increase the charge density of the grafted copolymer, allowing increased selectivity of binding or increased capacity of binding for negatively charged species, yet by virtue of not being salt-tolerant, will allow elution of the target species by a change in pH or salt concentration.
- the substrate for capture of target biological species may be any previously described, but is preferably a microporous membrane.
- the membrane pore size desired is from 0.1 to 10 ⁇ m, preferably 0.5 to 3 micrometers and most preferably 0.8 to 2 micrometers.
- a membrane with a high surface area for the internal pore structure is desired, which typically corresponds to fine pore sizes. However, if the pore size is too small, then the membrane tends to plug with fine particulates present in the sample solution.
- a filter element comprising one or more layers of the porous, ligand functionalized substrate.
- the individual layers may be the same or different, and may have layers of different porosity, and degree of grafting by the aforementioned grafting monomers.
- the filter element may further comprise an upstream prefilter layer and downstream support layer.
- the individual filter elements may be planar or pleated as desired.
- suitable prefilter and support layer materials include any suitable porous membranes of polypropylene, polyester, polyamide, resin-bonded or binder-free fibers (e.g., glass fibers), and other synthetics (woven and non-woven fleece structures); sintered materials such as polyolefins, metals, and ceramics; yarns; special filter papers (e.g., mixtures of fibers, cellulose, polyolefins, and binders); polymer membranes; and others.
- a filter cartridge including the above-described filter element.
- a filter assembly comprising the filter elements and a filter housing.
- this invention relates to a method of biological species capture comprising the steps of:
- Functionalized substrates were analyzed for static binding capacity by rocking one disk of the substrate in a solution of the test analyte overnight.
- the disk was prepared by die-punching a 24-mm diameter disk from a sheet of the substrate.
- Each disk was placed in a 5 mL centrifuge tube with 4.5 mL of BSA (bovine serum albumin) challenge solution (Catalog # A-7906) at a concentration of about 3.0 mg/ml in 25 millimolar TRIS (tris(hydroxymethyl)aminomethane) buffer, pH 8.0.
- BSA bovine serum albumin
- TRIS tris(hydroxymethyl)aminomethane
- the supernatant solutions were analyzed using a UV-VIS spectrometer at 279 nm (with background correction applied at 325 nm).
- the static binding capacity for each substrate was determined by comparison to the absorption of the starting BSA solution, and results are reported in mg/mL as the average of three replicates.
- Functionalized substrates were analyzed for dynamic binding of proteins by a passing solution of the test analyte through a 6-layer stack of the substrate.
- the stack was prepared by die-punching 25-mm diameter disks from a sheet of the substrate and placing the stack in a 25 mm diameter holder attached to an AKTA chromatography system (GE Healthcare, NY).
- BSA was prepared at a concentration 1 mg/mL in 25 millimolar TRIS buffer containing 50 millimolar NaCl, pH 8.0.
- the BSA challenge solution was pumped through the substrate stack at a flow rate of 1 mL/min and the UV absorbance of the effluent was monitored at a wavelength of 280 nm.
- the dynamic binding capacity of the substrate was evaluated using standard chromatography techniques, and reported in mg/mL at 10% breakthrough.
- Lysozyme (Catalog # L6876-10G) was prepared at a concentration of about 3.0 mg/mL in 10 millimolar MOPS (3-(N-morpholino) propanesulfonic acid,) buffer, pH 7.5.
- Functionalized substrates were analyzed as described for the Static BSA capacity method with for a challenge solution of human immunoglobulin (IgG) instead of BSA.
- Human IgG (Catalog # SLH66, Equitech-Bio, Kerrville Tex.) was prepared at a concentration of about 1.5 mg/mL in 50 millimolar sodium acetate with 40 millimolar NaCl buffer, pH 4.5.
- Polyethylenimine (PEI—MW 70,000, a 30% by weight aqueous solution, Cat#00618; Polysciences, Inc.; Warrington Pa.) was diluted to 1.0% solids with IPA (isopropanol). A 50 gram portion of this solution was formulated with enough butanediol diglycidyl ether (BUDGE, 106 microliter, Sigma Aldrich) to react with 5 mole % of the amine groups of the polymer.
- PIDGE butanediol diglycidyl ether
- Primed substrates were prepared by dipping a 10 square centimeter piece of a nylon 66 membrane (single reinforced layer nylon three zone membrane, nominal pore size 1.8 ⁇ m, #080ZN from 3M Purification, Inc.; Meridan Conn.), into the coating solution, removing excess coating solution with a #14 wire-wound coating rod, then allowing the substrate to air dry at ambient temperature for at least 15 minutes.
- a nylon 66 membrane single reinforced layer nylon three zone membrane, nominal pore size 1.8 ⁇ m, #080ZN from 3M Purification, Inc.; Meridan Conn.
- a priming solution and primed substrate were prepared as described for membrane substrate 1 except that enough glycidylmethacrylate was added to the polyethylenimine/butanediol diglycidyl ether priming solution to react with 10 mole % of the amine groups of the PEI polymer.
- Unprimed membrane substrate S3 was a nylon 66 membrane (single reinforced layer nylon three zone membrane, nominal pore size 1.8 ⁇ m, #080ZN from 3M Purification, Inc.; Meridan Conn.
- Substrate S4 was prepared according the procedure for the Preparation of Nylon Nonwoven Substrate A in U.S. Patent Publication No. 20100155323.
- the substrate was prepared to a basis weight of 60 grams per square meter (gsm) using 4.3 EFD Nylon B24 Nylon 6 polymer; BASF).
- Substrate S5 is a 50 gsm polypropylene SMS nonwoven web (4148 KiaraTM Filtration Media—20% 4-point square bond; PGI Polymers Inc., Mooresville N.C.). SMS indicates a layered construction having a layer of melt blown fibers laminated between two spun-bonded fiber layers.
- Membrane substrate S6 is a 4.5 mil thick polyethylene TIPS (thermally induced phase separation) membrane having a 1.30 micrometer pore size and 85% porosity that was prepared as described in U.S. Pat. No. 4,539,256.
- TIPS thermalally induced phase separation
- Membrane S7 is a 4.5 mil thick polypropylene TIPS membrane having a 0.80 micrometer pore size and 85% porosity that was prepared as described in U.S. Pat. Nos. 4,726,989, and 5,120,594.
- IEM-AGM sodium sulfate (4-(2-(methacryloyloxy)-ethylaminocarbonylamino)butylguanidinium sodium sulfate) was prepared according Example 99 of PCT Patent Publication Number US2012/024310, filed February 2012, which was based on U.S. Patent Application No. 61/468,302 filed Mar. 28, 2011.
- Coating solutions (5 grams each) were prepared in methanol from IEM-AGM sodium sulfate, MBA, and benzophenone in the amounts listed in Table 2.
- a 50 mg/mL solution of MBA in methanol and a 0.5 g/mL solution of benzophenone in methanol were first prepared. Portions of these solutions were micropipetted to each coating solution to obtain the desired amount of monomer and photoinitiator in the coating solution.
- Table 2 the amounts of IEM-AGM and benzophenone are listed as w/w % in the total solution, while MBA is listed as w/w % based on the amount of IEM-AGM.
- Primed substrates 51 were coated, grafted, and washed as described in Example 1. BSA binding capacities are shown in Table 1.
- Example 13 Coating solutions were prepared in methanol from IEM-AGM, MBA, and benzophenone as described above in Example 1.
- Example 13 also included 4.2% w/w PEG200 methacrylate as a co-monomer. Unprimed substrates S3 were coated, grafted, and washed as described in Example 1. BSA binding capacities are shown in Table 2.
- Coating solutions were prepared as described in Example 1, except the coating solvent was DI (deionized) water, and the benzophenone was replaced by S-BP (a water soluble benzophenone, 4-(3-sulfopropyloxyl)benzophenone, sodium salt prepared as described in Japanese patent 47040913). Substrates S3 were coated, grafted, and washed as described in Example 1. BSA binding capacities are shown in Table 3.
- Coating solutions were prepared as described in Example 13, except that portions of the IEM-AGM were replaced by dimethylacrylamide (DMA) or 2-hydroxyethylmethacrylate (HEMA). Substrates S3 were coated, grafted, washed and dried as described in Example 1. BSA binding capacities are shown in Table 4.
- Coating solutions were mixed having the compositions shown in Table 5. Each of the solutions included 2% w/w MBA based on total monomer weight and 0.5% w/w photoinitiator based on the total solution weight. Substrates were coated grafted washed and dried as in Example 1 except that Examples 48 and 49 were coated onto substrate S6, and Example 50 was coated onto substrate S7. BSA binding capacities are shown in Table 5.
- Coating solutions containing IEM-AGM (14% w/w) and PEG400 methacrylate (5.6% w/w) in methanol were prepared.
- Substrates S2 were coated, grafted, washed and dried as described in Example 1. BSA binding capacities are listed in Table 6.
- Coating solutions were prepared in 1:1 w/w methanol/DI water from VDM-AGM, sodium sulfate salt (N 2 -acryloyl-N 1 -(4- ⁇ [amino(imino)methyl]amino ⁇ butyl)-2-methylalaninamide) at the % solids shown in Table 7.
- the VDM-AGM was prepared as described in Applicant's copending U.S. Ser. No. 13/353,413, example 52. Each solution also contained 2% MBA based on the amount of VDM-AGM and 0.5% BP.
- Substrates S3 were coated and sandwiched between polyester sheets as described in Example 1.
- UV grafting was conducted using a UV stand (Classic Manufacturing, Inc., Oakdale, Minn.) equipped with 18 bulbs (Sylvania RG2 40W F40/350BL/ECO, 10 above and 8 below the substrate, 46 inches long, spaced 2 inches on center), with an irradiation time of 7 minutes. After grafting, the samples were washed, dried, and evaluated for BSA binding capacities. Results are shown in Table 7.
- a method of preparing a ligand functional substrate comprising the steps of:
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Pathology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Food Science & Technology (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
Description
wherein
R1 is H or C1-C4 alkyl;
R2 is a (hetero)hydrocarbyl group, preferably a divalent alkylene having 1 to 20 carbon atoms;
each R3 is independently H or hydrocarbyl, preferably C1-C12 alkyl;
R4 is H, C1-C12 alkyl or —N(R3)2;
R5 is H or hydrocarbyl, preferably C1-C12 alkyl or aryl;
X1 is —O— or —NR3—,
o is 0 or 1, and
n is 1 or 2.
wherein, Y is a straight or branched alkylene (e.g., an alkylenes having 1 to 10 carbon atoms, 1 to 6 carbon atoms, or 1 to 4 carbon atoms) and L is —O— or —NR3—, where R3 is H or C1-C12 alkyl; R1 is H or C1-C4 alkyl; and Y is an alkylene (e.g., an alkylene having 1 to 10 carbon atoms, 1 to 6, or 1 to 4 carbon atoms). Exemplary ionic monomers according to Formula 3 include, but are not limited to, N-acrylamidomethanesulfonic acid, 2-acrylamidoethanesulfonic acid, 2-acrylamido-2-methyl-1-propanesulfonic acid, and 2-methacrylamido-2-methyl-1-propanesulfonic acid. Salts of these acidic monomers can also be used. Counter ions for the salts can be, for example, ammonium ions, potassium ions, lithium ions, or sodium ions.
where L is —O— or —NR3—, where R1 is H or C1-C12 alkyl-; and Y is an alkylene (e.g., an alkylene having 1 to 10 carbon atoms, 1 to 6, or 1 to 4 carbon atoms). Each R11 is independently hydrogen, alkyl, hydroxyalkyl (i.e., an alkyl substituted with a hydroxy), or aminoalkyl (i.e., an alkyl substituted with an amino). Alternatively, the two R11 groups taken together with the nitrogen atom to which they are attached can form a heterocyclic group that is aromatic, partially unsaturated (i.e., unsaturated but not aromatic), or saturated, wherein the heterocyclic group can optionally be fused to a second ring that is aromatic (e.g., benzene), partially unsaturated (e.g., cyclohexene), or saturated (e.g., cyclohexane).
CH2═CR1—C(O)—X1—(CH(R1)—CH2—O)n—R1, 5
wherein each R1 is independently H or C1-C4 alkyl, X1 is —O— or —NR3—, where R3 is H or C1-C12 alkyl and n is 2 to 100.
-(MLig)y-(MHydrophil)x-(Mcrosslink)z-, 6
where
(MLig)y are guanidinyl ligand functional monomer units having “y” polymerized monomer units,
(MHydrophil)x are hydrophilic monomer units having “x” polymerized monomer units,
(Mcrosslink) are multifunctional (meth)acrylate monomer units having “z” polymerized monomer units,
y is 10 to 100 parts by weight of the (MLig) monomer units;
x is 0 to 90 parts by weight of the (Mhydrophil) monomer units;
z is 0 to 5 parts by weight of the (MCrosslink) monomer units, where the total is 100 parts by weight.
R8—(Z)y, 7
where R8 is a (hetero)hydrocarbyl group, Z is an amine-reactive group and y is ≧2, preferably 2-4. The R8 group may be an alkylene group, an arylene group, a heteroarylene group, a heteroalkylene group, an aralkylene group, or a combination thereof.
wherein
X1 is —O— or —NR3—, where R3 is H or C1-C12 alkyl,
R1 is H or C1-C4 alkyl;
R7 is a single bond or a (hetero)hydrocarbyl linking group,
A is a functional group that is reactive with the amino groups of the polyamine polymer, and
x is 0 or 1.
Ar—CO—R13 9
in which Ar is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms optionally substituted with a C1 to C12 alkyl group, a C1 to C12 alkoxy group, or a phenyl group; and R13 is a C1 to C6 alkyl group, a cycloalkyl group having 3 to 14 carbon atoms, or Ar
3) exposing the coated substrate (or imbibed porous base substrate) to UV radiation so as to form free radicals on the surface(s) of the base substrate by hydrogen abstraction, and graft-polymerizing the ethylenically unsaturated, free-radically polymerizable groups of the monomers onto the surface of the base substrate.
TABLE 1 | ||||
Exam- | IEM-AGM | MBA | benzophenone | BSA Capacity (mg/mL) |
ple | (w/w %) | % | (w/w %) | Static | Dynamic |
4 | 14 | 0 | 0.1 | 57 | Not determined |
5 | 14 | 1 | 0.1 | 101 | 78 |
6 | 14 | 2 | 0.1 | 116 | 89 |
7 | 14 | 3 | 0.1 | 133 | 81 |
8 | 16 | 2 | 0.1 | 118 | 88 |
9 | 18 | 2 | 0.5 | 103 | 87 |
TABLE 2 | ||||
Exam- | IEM-AGM | MBA | Benzophenone | BSA Capacity (mg/mL) |
ple | (w/w %) | % | (w/w %) | Static | Dynamic |
7 | 14 | 2 | 2 | 138 | 102 |
8 | 14 | 2 | 1 | 136 | 74 |
9 | 14 | 2 | 0.5 | 135 | 100 |
10 | 14 | 2 | 0.1 | 142 | 71 |
11 | 12 | 2 | 0.5 | 111 | 79 |
12 | 10 | 2 | 0.5 | 102 | 64 |
13 | 14 | 2 | 0.5 | 112 | 102 |
TABLE 3 | ||||
Exam- | IEM-AGM | MBA | S-BP | BSA Capacity (mg/mL) |
ple | (w/w %) | % | (w/w %) | Static | Dynamic |
14 | 14 | 2 | 2 | 39 | 27 |
15 | 14 | 2 | 1 | 51 | 30 |
16 | 14 | 2 | 0.5 | 69 | 40 |
17 | 14 | 2 | 0.1 | 73 | 37 |
TABLE 4 | ||||
Exam- | IEM-AGM | DMA | HEMA | BSA Capacity (mg/mL) |
ple | (w/w %) | (w/w %) | (w/w %) | Static | Dynamic |
18 | 12 | 2 | — | 137 | 85 |
19 | 10 | 4 | — | 141 | 72 |
20 | 8 | 6 | — | 132 | 58 |
21 | 6 | 8 | — | 101 | 39 |
22 | 12 | — | 2 | 135 | 87 |
23 | 10 | — | 4 | 131 | 78 |
24 | 8 | — | 6 | 132 | 61 |
25 | 6 | — | 8 | 103 | 41 |
TABLE 5 | ||||
IEM-AGM | Static BSA Capacity | |||
Ex | (w/w %) | Solvent | Photoinitiator | (mg/mL) |
26 | 14 | Methanol | BP | 109 |
27 | 14 | Methanol | BP | 93 |
TABLE 6 | ||||
Exam- | MBA | BP | BSA Capacity (mg/mL) |
ple | (%) | (w/w %) | Static | Dynamic |
28 | 3 | 0.125 | 144 | 82 |
29 | 3 | 0.500 | 135 | 83 |
30 | 2 | 0.250 | 143 | 89 |
31 | 1 | 0.125 | 137 | 95 |
32 | 1 | 0.500 | 137 | 92 |
33 | 0 | 0.125 | 125 | 93 |
34 | 0 | 0.250 | 129 | 117 |
35 | 0 | 0.500 | 125 | 113 |
TABLE 7 | |||||
Exam- | VDM-AGM | BSA Capacity (mg/mL) |
ple | (w/w %) | Static | Dynamic | ||
36 | 8 | 67 | 44 | ||
37 | 10 | 91 | 56 | ||
38 | 12 | 116 | 78 | ||
39 | 14 | 131 | 89 | ||
40 | 16 | 145 | 91 | ||
This disclosure provides the following embodiments:
1. A method of preparing a ligand functional substrate comprising the steps of:
-
- a) providing a substrate,
- b) free-radically grafting the substrate in the presence of a Type II photoinitiator with a guanidinyl-functional (meth)acryloyl monomer of the formula:
-
- wherein
- R1 is H or C1-C4 alkyl;
- R2 is a (hetero)hydrocarbyl group;
- each R3 is independently H or hydrocarbyl;
- R4 is H, C1-C12 alkyl or —N(R3)2;
- R5 is H or hydrocarbyl;
- X1 is —O— or —NR3—;
- o is 0 or 1, and
- n is 1 or 2.
2. The method of embodiment 1 wherein the substrate is provided with a primer layer disposed on the substrate comprising the reaction product of: - 1) a polyamine polymer; and
- 2) a polyfunctional crosslinking agent for the polyamine polymer.
3. The method of embodiment 1 wherein the substrate is provided with a primer layer disposed on the substrate comprising the reaction product of: - 1) a polyamine polymer;
- 2) a polyfunctional crosslinking agent for the polyamine polymer; and
- 3) an amine-reactive monomer having an amine-reactive functional group and an ethylenically unsaturated, polymerizable group, to provide a substrate having a crosslinked polyamine primer layer on the substrate, the primer layer having pendent alkenyl groups.
4. The method of any of the previous embodiments further comprising grafting the substrate with a hydrophilic monomer.
5. The method of any of the previous embodiments further comprising grafting with a multifunctional (meth)acryloyl monomer.
6. The method of any of the previous embodiments wherein the Type II photoinitiator is a benzophenone photoinitiator.
7. The method of embodiment 6 wherein the benzophenone photoinitiator is water-soluble.
8. The method of any of the previous embodiments comprising the step of imbibing the substrate with a monomer mixture comprising: - a) up to 100 parts by weight of guanidinyl monomers,
- b) 0 to 90 parts by weight of hydrophilic monomer units, and
- c) 0 to about 5 by weight parts by weight of multifunctional (meth)acryloyl monomer wherein the total monomer is 100 parts by weight.
9. The method of embodiment 8 wherein the imbibing monomer mixture comprises about 0.1 wt % to about 60 wt % of monomers in an organic or aqueous solvent.
10. The method of any of the previous embodiments wherein the grafted monomers form a grafted copolymer of the formula:
-(MLig)y-(MHydrophil)x-(Mcrosslink)z-, where - (MHydrophil)x are hydrophilic monomer units having “x” polymerized monomer units, (MLig)y are ligand functional monomer units having “y” polymerized monomer units, (Mcrosslink) are multifunctional (meth)acrylate monomer units having “z” polymerized monomer units.
11. The method of embodiment 4 wherein the hydrophilic monomer units comprise poly(oxyalkylene) (meth)acrylate monomer units.
12. The ligand-functional substrate of embodiment 11, wherein the poly(oxyalkylene) (meth)acrylate monomer units are of the formula: CH2═CR1—C(O)—X1—(CH(R1)—CH2—O)n—R1, wherein each R1 is independently H or C1-C4 alkyl, X1 is —O— or —NR3—, where R3 is H or C1-C4 alkyl and n is 2 to 100.
13. The method of embodiment 1 wherein the substrate comprises a primer layer disposed on the substrate comprising a crosslinked polyamine polymer having ethylenically unsaturated polymerizable groups.
14. The method of embodiment 13 wherein the crosslinked polyamine polymer having ethylenically unsaturated polymerizable groups is the reaction product of: - 1) a polyamine polymer;
- 2) a polyfunctional crosslinking agent for the polyamine polymer; and
- 3) a monomer having an amine-reactive functional group and an ethylenically unsaturated polymerizable group.
15. The method of any of the previous embodiments wherein the polyamine polymer is selected from the group consisting of polyethylenimine, polylysine, polyaminoamides, polydimethylamine-epichlorohydrin-ethylenediamine, polyaminosiloxanes and dendrimers formed from polyamidoamine (PAMAM) and polypropylenimine.
16. The method of any of the previous embodiments wherein said primer layer comprises 0.1 to 5 wt. % of the substrate.
17. The method of embodiment 10 wherein said (co)polymer comprises 5 to 30 wt. % of the ligand functional substrate.
18. A method of separating a target biological species from a fluid comprising contacting the fluid with the ligand-functionalized substrate prepared by the method of any of the previous embodiments whereby a complex comprising the functionalized substrate and the target biological species is formed, and separating the complex; wherein said target biological species is selected from biomacromolecules and microbiological species.
19. The method of embodiment 18 wherein said biomacromolecules are selected from proteins, enzymes, nucleic acids, and endotoxins.
20. The method of embodiment 18 wherein said microbiological species is selected from bacteria, viruses, cells, cell debris, and spores.
21. The method of embodiment 20 wherein the cells are selected from archaea, bacteria, and eucaryota.
22. The method of embodiments 18 to 21 wherein the biological fluid is derived from a cell culture or fermentation process.
23. The method of embodiments 18 to 21 wherein the biological fluid comprises a solution of a purified protein or enzyme after separating the target species.
24. The method of embodiment 23 wherein the separated target species comprises a purified protein or enzyme.
25. The method of embodiments 18 to 21 wherein the fluid has a salt content of at least 50 millimolar.
26. An article comprising: - a) a substrate, and
- b) grafted to the surface of the substrate (co)polymer comprising interpolymerized of guanidinyl-functional (meth)acryloyl monomer units of the formula:
-
- wherein
- R1 is H or C1-C4 alkyl;
- R2 is a (hetero)hydrocarbyl group;
- each R3 is independently H or hydrocarbyl;
- R4 is H, C1-C12 alkyl or —N(R3)2;
- R5 is H or hydrocarbyl;
- X1 is —O— or —NR3—;
- o is 0 or 1, and
- n is 1 or 2.
27. The article of embodiment 26 wherein the grafted copolymer further comprises hydrophilic monomer units.
28. The article of embodiment 26 wherein the grafted polymer comprises: - a) up to 100 parts by weight of guanidinyl monomers,
- b) 0 to 90 parts by weight of hydrophilic monomer units, and
- c) 0 parts by weight of multifunctional (meth)acryloyl monomer
- wherein the total monomer is 100 parts by weight.
29. The article of embodiment 26 wherein the grafted copolymer is of the formula:
-(MLig)y-(Mhydrophil)x-, where - (Mhydrophil)x are hydrophilic monomer units having “x” polymerized monomer units, and
- (MLig)y are guanidinyl functional ligand monomer units having “y” polymerized monomer units.
30. The article of any of embodiments 26-29 wherein the hydrophilic monomer units comprise poly(oxyalkylene) (meth)acrylate monomer units.
31. The ligand-functional substrate of embodiment 30, wherein the poly(oxyalkylene) (meth)acrylate monomer units are of the formula: CH2═CR1—C(O)—X1—(CH(R1)—CH2—O)n—R1, wherein each R1 is independently H or C1-C4 alkyl, X1 is —O— or —NR3—, where R3 is H or C1-C4 alkyl and n is 2 to 100.
32. The ligand-functional substrate of any of embodiments 26-31 wherein the grafted (co)polymer is uncrosslinked.
Claims (23)
Ar—CO—R13
-(MLig)y-(MHydrophil)x-(Mcrosslink)z-, where
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/400,810 US9616394B2 (en) | 2012-06-05 | 2013-05-23 | Graft copolymer functionalized article |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201261655516P | 2012-06-05 | 2012-06-05 | |
US14/400,810 US9616394B2 (en) | 2012-06-05 | 2013-05-23 | Graft copolymer functionalized article |
PCT/US2013/042330 WO2013184366A1 (en) | 2012-06-05 | 2013-05-23 | Graft copolymer functionalized article |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2013/042330 A-371-Of-International WO2013184366A1 (en) | 2012-06-05 | 2013-05-23 | Graft copolymer functionalized article |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/444,565 Division US10471398B2 (en) | 2012-06-05 | 2017-02-28 | Graft copolymer functionalized article |
Publications (2)
Publication Number | Publication Date |
---|---|
US20150136698A1 US20150136698A1 (en) | 2015-05-21 |
US9616394B2 true US9616394B2 (en) | 2017-04-11 |
Family
ID=48576587
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/400,810 Active 2034-01-26 US9616394B2 (en) | 2012-06-05 | 2013-05-23 | Graft copolymer functionalized article |
US15/444,565 Active 2033-06-26 US10471398B2 (en) | 2012-06-05 | 2017-02-28 | Graft copolymer functionalized article |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/444,565 Active 2033-06-26 US10471398B2 (en) | 2012-06-05 | 2017-02-28 | Graft copolymer functionalized article |
Country Status (5)
Country | Link |
---|---|
US (2) | US9616394B2 (en) |
EP (2) | EP3326711B1 (en) |
JP (1) | JP6257605B2 (en) |
CN (1) | CN104736235B (en) |
WO (1) | WO2013184366A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2020127311A1 (en) | 2018-12-17 | 2020-06-25 | Chreto Aps | Ligand linker substrate |
US10913807B2 (en) | 2017-12-21 | 2021-02-09 | 3M Innovative Properties Company | Polymeric compositions prepared with a controlled radical initiator |
WO2021105843A1 (en) | 2019-11-25 | 2021-06-03 | 3M Innovative Properties Company | Biotin-containing monomers and articles formed therefrom |
WO2021209859A1 (en) | 2020-04-14 | 2021-10-21 | 3M Innovative Properties Company | Monomers, polymers, and articles for biomaterial capture |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105308021B (en) | 2013-06-17 | 2018-05-04 | 3M创新有限公司 | It is used to prepare the method for guanidine radicals functionalized monomer |
US9475894B2 (en) * | 2013-06-25 | 2016-10-25 | China Petroleum & Chemical Corporation | Dendritic polymer, dendritic polymer monomer, and hyperbranched copolymer |
CN105338815B (en) * | 2013-06-28 | 2020-07-14 | 3M创新有限公司 | Wipes with guanidino-containing polymers |
WO2015050767A1 (en) * | 2013-10-03 | 2015-04-09 | 3M Innovative Properties Company | Ligand-functionalized substrates with enhanced binding capacity |
JP6157751B2 (en) * | 2013-12-19 | 2017-07-05 | スリーエム イノベイティブ プロパティズ カンパニー | LAMINATED ARTICLE FOR MICROBODY REMOVAL AND LOW PRESSURE LOW FILTRATION, PROCESS FOR PRODUCING THE SAME |
JP6606182B2 (en) | 2014-09-08 | 2019-11-13 | スリーエム イノベイティブ プロパティズ カンパニー | Ionic polymer membrane for carbon dioxide electrolyzer |
SG11201704043VA (en) * | 2014-11-20 | 2017-06-29 | Entegris Inc | Grafted ultra high molecular weight polyethylene microporous membranes |
WO2016153915A1 (en) | 2015-03-24 | 2016-09-29 | 3M Innovative Properties Company | Method of purifying a biological composition and article therefor |
JP6878318B2 (en) | 2015-06-26 | 2021-05-26 | インテグリス・インコーポレーテッド | Grafted polysulfone membrane |
BR112018008250B1 (en) * | 2015-10-23 | 2022-10-04 | 3M Innovative Properties Company | SEQUENCE OF FILTERING MEDIUM, FILTERING DEVICE AND MANUFACTURING METHOD OF A BIOLOGICAL FLUID |
CN109689674A (en) | 2016-09-09 | 2019-04-26 | 3M创新有限公司 | From the method for the monomeric protein separation collectin matter in biological solution |
CN109689189B (en) * | 2016-09-09 | 2022-02-01 | 3M创新有限公司 | Functionalized copolymers and uses thereof |
EP3565411A4 (en) * | 2017-01-04 | 2020-07-01 | 3M Innovative Properties Company | Methods of removing spores |
CN110167515A (en) * | 2017-01-04 | 2019-08-23 | 3M创新有限公司 | The method for removing spore |
NL2019044B1 (en) * | 2017-05-11 | 2018-11-15 | Illumina Inc | Protective surface coatings for flow cells |
US10596525B2 (en) * | 2017-08-07 | 2020-03-24 | United States Of America As Represented By The Secretary Of The Army | Advanced filtration membranes using chitosan and graphene oxide |
US11421261B2 (en) | 2017-12-19 | 2022-08-23 | 3M Innovative Properties Company | Methods to detect microorganisms |
US11390722B2 (en) | 2017-12-20 | 2022-07-19 | 3M Innovative Properties Company | Polymeric substrates with attached thiocarbonylthio-containing groups |
EP3728425B1 (en) | 2017-12-20 | 2021-12-08 | 3M Innovative Properties Company | Polymeric substrates with attached polymeric chains |
US11045773B2 (en) * | 2018-08-31 | 2021-06-29 | Pall Corporation | Salt tolerant porous medium |
US10737259B2 (en) * | 2018-08-31 | 2020-08-11 | Pall Corporation | Salt tolerant anion exchange medium |
CN109569331B (en) * | 2018-12-18 | 2021-10-22 | 万华化学集团股份有限公司 | Preparation method of hydrophilic antibacterial filter membrane |
CN114173560B (en) * | 2019-08-07 | 2024-07-09 | 舒万诺知识产权公司 | Articles comprising crosslinked guanidine-containing polymers and uses thereof |
CN111185168B (en) * | 2020-01-14 | 2023-02-03 | 上海华谊(集团)公司 | Nano gold catalyst, preparation and application thereof |
CN112808022B (en) * | 2020-12-31 | 2022-10-21 | 太原科技大学 | Polyvinyl amine membrane with hydrophilic and hydrophobic functional groups and preparation method and application thereof |
US20240207765A1 (en) * | 2021-04-30 | 2024-06-27 | 3M Innovative Properties Company | Viral filtration media, articles, and methods |
CN113457449B (en) * | 2021-07-26 | 2022-05-24 | 中国海洋大学 | Polyamide nanofiltration membrane with multivalent/monovalent salt selectivity and preparation method thereof |
WO2023089412A1 (en) | 2021-11-19 | 2023-05-25 | 3M Innovative Properties Company | Method for biomaterial purification |
CN114878727B (en) * | 2022-05-06 | 2023-07-25 | 合肥高尔生命健康科学研究院有限公司 | Method for determining hymexazol residues in tobacco |
WO2023248020A1 (en) | 2022-06-23 | 2023-12-28 | 3M Innovative Properties Company | Block copolymers grafted to porous polymeric substrate |
CN115888182A (en) * | 2022-10-13 | 2023-04-04 | 福州大学 | Strong cationic charge type aptamer functionalized high-hydrophilicity affinity monolithic column |
CN117904899B (en) * | 2024-03-20 | 2024-05-24 | 沈阳森和盛源木业有限公司 | Preparation method of modified melamine impregnated paper |
Citations (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3018262A (en) | 1957-05-01 | 1962-01-23 | Shell Oil Co | Curing polyepoxides with certain metal salts of inorganic acids |
US3298998A (en) | 1961-03-07 | 1967-01-17 | Eastman Kodak Co | Bisglycidyl ethers of bisphenols |
US3876738A (en) | 1973-07-18 | 1975-04-08 | Amf Inc | Process for producing microporous films and products |
US3928517A (en) | 1973-12-26 | 1975-12-23 | Amf Inc | Quench bath regeneration system for microporous film production |
US4157418A (en) | 1978-02-08 | 1979-06-05 | Minnesota Mining And Manufacturing Company | Acrylic functional aminocarboxylic acids and derivatives as components of pressure sensitive adhesives |
US4539256A (en) | 1982-09-09 | 1985-09-03 | Minnesota Mining And Manufacturing Co. | Microporous sheet material, method of making and articles made therewith |
US4707265A (en) | 1981-12-18 | 1987-11-17 | Cuno Incorporated | Reinforced microporous membrane |
US4726989A (en) | 1986-12-11 | 1988-02-23 | Minnesota Mining And Manufacturing | Microporous materials incorporating a nucleating agent and methods for making same |
US4867881A (en) | 1987-09-14 | 1989-09-19 | Minnesota Minning And Manufacturing Company | Orientied microporous film |
US5039549A (en) | 1989-10-17 | 1991-08-13 | Allied-Signal Inc. | Treatment of ultrahigh molecular weight polyolefin to improve adhesion to a resin |
US5120594A (en) | 1989-11-20 | 1992-06-09 | Minnesota Mining And Manufacturing Company | Microporous polyolefin shaped articles with patterned surface areas of different porosity |
US5260360A (en) | 1991-10-18 | 1993-11-09 | Minnesota Mining And Manufacturing Company | Oil, water and sweat repellent microporous membrane materials |
US5458782A (en) | 1994-01-07 | 1995-10-17 | Cuno Incorporated | Hydrolytically stable nylon membrane |
WO1997002313A1 (en) | 1995-06-30 | 1997-01-23 | Institutet Polymerutveckling Ab | Lamination by photografting |
US5962544A (en) | 1995-12-07 | 1999-10-05 | 3M | Microporous materials of ethylene-vinyl alcohol copolymer and methods for making same |
US6056529A (en) | 1998-02-11 | 2000-05-02 | Cuno, Inc. | Systems for producing a plurality of different microporous phase inversion membrane each having any one of a plurality of different pore sizes from a single master dope batch |
US6413070B1 (en) | 1997-04-11 | 2002-07-02 | Cuno Incorporated | System for manufacturing reinforced three-zone microporous membrane |
US20050142563A1 (en) | 2003-12-24 | 2005-06-30 | 3M Innovative Properties Company | Materials, methods, and kits for reducing nonspecific binding of molecules to a surface |
US7125603B2 (en) | 2001-12-14 | 2006-10-24 | 3M Innovative Properties Company | Plasma treatment of porous materials |
US7338692B2 (en) | 2003-09-12 | 2008-03-04 | 3M Innovative Properties Company | Microporous PVDF films |
US7556858B2 (en) | 2004-09-30 | 2009-07-07 | 3M Innovative Properties Company | Substrate with attached dendrimers |
WO2009148869A1 (en) | 2008-05-30 | 2009-12-10 | 3M Innovative Properties Company | Method of making ligand functionalized substrates |
US20100155323A1 (en) | 2008-12-23 | 2010-06-24 | Weiss Douglas E | Functionalized nonwoven article |
WO2011109151A1 (en) | 2010-03-03 | 2011-09-09 | 3M Innovative Properties Company | Ligand guanidinyl functionalized polymers |
WO2012134636A1 (en) | 2011-03-28 | 2012-10-04 | 3M Innovative Properties Company | Ligand functional substrates |
US20150203645A1 (en) * | 2012-09-27 | 2015-07-23 | 3M Innovative Properties Company | Ligand grafted substrates |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3146913C2 (en) | 1981-11-26 | 1983-10-06 | C.A. Weidmueller Gmbh & Co, 4930 Detmold | Cross connector |
JPH0740913B2 (en) | 1986-10-29 | 1995-05-10 | 株式会社リブ・インタ−ナシヨナル | How to adjust the quality of liquor |
SE500503C2 (en) | 1990-12-07 | 1994-07-04 | Inst Polymerutveckling Ab | Method and irradiation unit for continuous cross-linking of polyethylene |
EP1693101A1 (en) * | 2005-02-11 | 2006-08-23 | Paul Scherrer Institut | A method for preparing a radiation grafted fuel cell membrane with enhanced chemical stability and a membrane electrode assembly |
JP2011523965A (en) * | 2008-05-30 | 2011-08-25 | スリーエム イノベイティブ プロパティズ カンパニー | Ligand functionalized substrate |
US8377672B2 (en) * | 2010-02-18 | 2013-02-19 | 3M Innovative Properties Company | Ligand functionalized polymers |
-
2013
- 2013-05-23 US US14/400,810 patent/US9616394B2/en active Active
- 2013-05-23 JP JP2015516041A patent/JP6257605B2/en active Active
- 2013-05-23 EP EP17205059.3A patent/EP3326711B1/en active Active
- 2013-05-23 CN CN201380029528.5A patent/CN104736235B/en active Active
- 2013-05-23 WO PCT/US2013/042330 patent/WO2013184366A1/en active Application Filing
- 2013-05-23 EP EP13726995.7A patent/EP2855010B1/en active Active
-
2017
- 2017-02-28 US US15/444,565 patent/US10471398B2/en active Active
Patent Citations (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3018262A (en) | 1957-05-01 | 1962-01-23 | Shell Oil Co | Curing polyepoxides with certain metal salts of inorganic acids |
US3298998A (en) | 1961-03-07 | 1967-01-17 | Eastman Kodak Co | Bisglycidyl ethers of bisphenols |
US3876738A (en) | 1973-07-18 | 1975-04-08 | Amf Inc | Process for producing microporous films and products |
US3928517A (en) | 1973-12-26 | 1975-12-23 | Amf Inc | Quench bath regeneration system for microporous film production |
US4157418A (en) | 1978-02-08 | 1979-06-05 | Minnesota Mining And Manufacturing Company | Acrylic functional aminocarboxylic acids and derivatives as components of pressure sensitive adhesives |
US4707265A (en) | 1981-12-18 | 1987-11-17 | Cuno Incorporated | Reinforced microporous membrane |
US4539256A (en) | 1982-09-09 | 1985-09-03 | Minnesota Mining And Manufacturing Co. | Microporous sheet material, method of making and articles made therewith |
US4726989A (en) | 1986-12-11 | 1988-02-23 | Minnesota Mining And Manufacturing | Microporous materials incorporating a nucleating agent and methods for making same |
US4867881A (en) | 1987-09-14 | 1989-09-19 | Minnesota Minning And Manufacturing Company | Orientied microporous film |
US5039549A (en) | 1989-10-17 | 1991-08-13 | Allied-Signal Inc. | Treatment of ultrahigh molecular weight polyolefin to improve adhesion to a resin |
US5120594A (en) | 1989-11-20 | 1992-06-09 | Minnesota Mining And Manufacturing Company | Microporous polyolefin shaped articles with patterned surface areas of different porosity |
US5260360A (en) | 1991-10-18 | 1993-11-09 | Minnesota Mining And Manufacturing Company | Oil, water and sweat repellent microporous membrane materials |
US5458782A (en) | 1994-01-07 | 1995-10-17 | Cuno Incorporated | Hydrolytically stable nylon membrane |
WO1997002313A1 (en) | 1995-06-30 | 1997-01-23 | Institutet Polymerutveckling Ab | Lamination by photografting |
US5962544A (en) | 1995-12-07 | 1999-10-05 | 3M | Microporous materials of ethylene-vinyl alcohol copolymer and methods for making same |
US6413070B1 (en) | 1997-04-11 | 2002-07-02 | Cuno Incorporated | System for manufacturing reinforced three-zone microporous membrane |
US6776940B2 (en) | 1997-04-11 | 2004-08-17 | Cuno Incorporated | Process for making a three-zone microporous membrane |
US6267916B1 (en) | 1998-02-11 | 2001-07-31 | Cuno, Inc. | Process of making microporous phase inversion membranes |
US6056529A (en) | 1998-02-11 | 2000-05-02 | Cuno, Inc. | Systems for producing a plurality of different microporous phase inversion membrane each having any one of a plurality of different pore sizes from a single master dope batch |
US7125603B2 (en) | 2001-12-14 | 2006-10-24 | 3M Innovative Properties Company | Plasma treatment of porous materials |
US7338692B2 (en) | 2003-09-12 | 2008-03-04 | 3M Innovative Properties Company | Microporous PVDF films |
US20050142563A1 (en) | 2003-12-24 | 2005-06-30 | 3M Innovative Properties Company | Materials, methods, and kits for reducing nonspecific binding of molecules to a surface |
US7556858B2 (en) | 2004-09-30 | 2009-07-07 | 3M Innovative Properties Company | Substrate with attached dendrimers |
WO2009148869A1 (en) | 2008-05-30 | 2009-12-10 | 3M Innovative Properties Company | Method of making ligand functionalized substrates |
US20100155323A1 (en) | 2008-12-23 | 2010-06-24 | Weiss Douglas E | Functionalized nonwoven article |
WO2011109151A1 (en) | 2010-03-03 | 2011-09-09 | 3M Innovative Properties Company | Ligand guanidinyl functionalized polymers |
WO2012134636A1 (en) | 2011-03-28 | 2012-10-04 | 3M Innovative Properties Company | Ligand functional substrates |
US20120252091A1 (en) | 2011-03-28 | 2012-10-04 | 3M Innovative Properties Company | Ligand functional substrates |
US20150203645A1 (en) * | 2012-09-27 | 2015-07-23 | 3M Innovative Properties Company | Ligand grafted substrates |
Non-Patent Citations (8)
Title |
---|
International Search Report for PCT International Application No. PCT/US2013/042330, mailed on Aug. 16, 2013, 4 pages. |
Oster, "Ultraviolet Induced Crosslinking and Grafting of Solid High Polymers", Journal of Polymer Science, 1959, vol. 34, pp. 671-684. |
Ranby, "Modification of Polymer Surfaces by Photoinduced Graft Copolymerization", Chemical Reactions on Polymers, 168-186 (2009). |
Rasmussen, "Polyazlactones", Encyclopedia of Polymer Science and Engineering, 558-571 (1988). |
Rohr, "Surface Functionalization of Thermoplastic Polymers for the Fabrication of Microfluidic Devices by Photoinitiated Grafting", Advanced Functional Materials, Apr. 2003, vol. 13, No. 4, pp. 264-270. |
Tasdelen, "Poly (propylene imine) dendrimers as hydrogen donor in Type II photoinitiated free radical polymerization", European Polymer Journal, 2007, vol. 43, pp. 4423-4430. |
Wente, "Manufacture of Superfine Organic Fibers", Naval Research Laboratories Report No. 4364, May 25, 1954, 23 pages. |
Wente, "Superfine Thermoplastic Fibers", Industrial and Engineering Chemistry, Aug. 1956, vol. 48, No. 8, pp. 1342-1346. |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10913807B2 (en) | 2017-12-21 | 2021-02-09 | 3M Innovative Properties Company | Polymeric compositions prepared with a controlled radical initiator |
WO2020127311A1 (en) | 2018-12-17 | 2020-06-25 | Chreto Aps | Ligand linker substrate |
EP4134157A1 (en) | 2018-12-17 | 2023-02-15 | CHRETO ApS | Use of ligand linker substrate for purification |
EP4134158A1 (en) | 2018-12-17 | 2023-02-15 | 3M Innovative Properties Company | Ligand linker substrate |
WO2021105843A1 (en) | 2019-11-25 | 2021-06-03 | 3M Innovative Properties Company | Biotin-containing monomers and articles formed therefrom |
WO2021209859A1 (en) | 2020-04-14 | 2021-10-21 | 3M Innovative Properties Company | Monomers, polymers, and articles for biomaterial capture |
Also Published As
Publication number | Publication date |
---|---|
US20170165617A1 (en) | 2017-06-15 |
EP3326711A1 (en) | 2018-05-30 |
US20150136698A1 (en) | 2015-05-21 |
CN104736235A (en) | 2015-06-24 |
EP3326711B1 (en) | 2021-07-07 |
CN104736235B (en) | 2017-10-13 |
JP2015521229A (en) | 2015-07-27 |
WO2013184366A1 (en) | 2013-12-12 |
EP2855010A1 (en) | 2015-04-08 |
EP2855010B1 (en) | 2017-12-27 |
US10471398B2 (en) | 2019-11-12 |
JP6257605B2 (en) | 2018-01-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US10471398B2 (en) | Graft copolymer functionalized article | |
US11279731B2 (en) | Ligand functional substrates | |
US9981244B2 (en) | Ligand grafted substrates | |
US20200102345A1 (en) | Ligand functionalized polymers | |
US9492771B2 (en) | Ligand graft functionalized substrates | |
US7067058B2 (en) | Hydrophilic membrane and process for making the same | |
Seshadri et al. | Etzel et al. |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: 3M INNOVATIVE PROPERTIES COMPANY, MINNESOTA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:BOTHOF, CATHERINE A.;GRIESGRABER, GEORGE W.;RASMUSSEN, JERALD K.;SIGNING DATES FROM 20141029 TO 20141030;REEL/FRAME:034162/0094 |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
CC | Certificate of correction | ||
MAFP | Maintenance fee payment |
Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY Year of fee payment: 4 |
|
AS | Assignment |
Owner name: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY, MINNESOTA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:3M INNOVATIVE PROPERTIES COMPANY;REEL/FRAME:066430/0287 Effective date: 20240201 |